HU192451B - Process for preparing alpha-sulphonyl-oxy- ketone-acetal derivatives - Google Patents

Process for preparing alpha-sulphonyl-oxy- ketone-acetal derivatives Download PDF

Info

Publication number: HU192451B
Authority: HU; Hungary
Prior art keywords: formula; defined above; compound; phenyl; alkyl
Prior art date: 1980-09-11

Application number

HU843583A

Other languages

English (en)

Hungarian (hu)

Inventor

Genichi Tsuchihashi

Shuichi Mitamura

Kouji Kitajima

Original Assignee

Syntex Pharma Int

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1980-09-11

Filing date

1981-09-09

Publication date

1987-06-29

1980-09-11 Priority claimed from JP55125355A external-priority patent/JPS5750956A/ja

1980-10-15 Priority claimed from JP55143042A external-priority patent/JPS5767535A/ja

1981-09-09 Application filed by Syntex Pharma Int filed Critical Syntex Pharma Int

1987-06-29 Publication of HU192451B publication Critical patent/HU192451B/hu

Links

238000004519 manufacturing process Methods 0.000 title 1
-1 C 1 -C 4 alkyl Chemical group 0.000 claims abstract description 87
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 26
125000000217 alkyl group Chemical group 0.000 claims abstract description 16
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims abstract description 13
229910052736 halogen Inorganic materials 0.000 claims abstract description 12
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
238000000034 method Methods 0.000 claims abstract description 10
150000002367 halogens Chemical class 0.000 claims abstract description 9
239000001257 hydrogen Substances 0.000 claims abstract description 9
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims abstract description 8
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 7
238000002360 preparation method Methods 0.000 claims abstract description 6
125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 4
125000001153 fluoro group Chemical group F* 0.000 claims abstract description 4
150000001875 compounds Chemical class 0.000 claims description 91
229910052783 alkali metal Inorganic materials 0.000 claims description 30
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 24
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 22
206010029897 Obsessive thoughts Diseases 0.000 claims description 8
150000001340 alkali metals Chemical class 0.000 claims description 8
239000004593 Epoxy Substances 0.000 claims description 6
125000005843 halogen group Chemical group 0.000 claims description 5
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 4
FCSKOFQQCWLGMV-UHFFFAOYSA-N 5-{5-[2-chloro-4-(4,5-dihydro-1,3-oxazol-2-yl)phenoxy]pentyl}-3-methylisoxazole Chemical compound O1N=C(C)C=C1CCCCCOC1=CC=C(C=2OCCN=2)C=C1Cl FCSKOFQQCWLGMV-UHFFFAOYSA-N 0.000 claims description 3
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 3
125000005059 halophenyl group Chemical group 0.000 claims description 3
239000003513 alkali Substances 0.000 claims description 2
150000004703 alkoxides Chemical class 0.000 claims description 2
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
125000004432 carbon atom Chemical group C* 0.000 abstract description 2
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 abstract 2
DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 abstract 1
241000723346 Cinnamomum camphora Species 0.000 abstract 1
229960000846 camphor Drugs 0.000 abstract 1
229930008380 camphor Natural products 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 66
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 60
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 50
239000000047 product Substances 0.000 description 48
239000000203 mixture Substances 0.000 description 47
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 46
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 39
238000006243 chemical reaction Methods 0.000 description 28
239000007858 starting material Substances 0.000 description 27
SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 24
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 23
239000002904 solvent Substances 0.000 description 21
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 20
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 18
238000004458 analytical method Methods 0.000 description 18
239000013078 crystal Substances 0.000 description 17
239000000284 extract Substances 0.000 description 16
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 13
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 12
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
238000000746 purification Methods 0.000 description 11
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 10
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 10
238000004440 column chromatography Methods 0.000 description 10
238000001816 cooling Methods 0.000 description 10
230000007062 hydrolysis Effects 0.000 description 10
238000006460 hydrolysis reaction Methods 0.000 description 10
229910000027 potassium carbonate Inorganic materials 0.000 description 10
229940093956 potassium carbonate Drugs 0.000 description 10
235000011181 potassium carbonates Nutrition 0.000 description 10
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
229940123973 Oxygen scavenger Drugs 0.000 description 9
FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 9
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 8
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 8
KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 8
238000001228 spectrum Methods 0.000 description 8
238000003756 stirring Methods 0.000 description 8
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 8
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 7
229910052708 sodium Inorganic materials 0.000 description 7
239000011734 sodium Substances 0.000 description 7
238000010626 work up procedure Methods 0.000 description 7
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
239000000460 chlorine Substances 0.000 description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
GIFLQCVVIWXBBS-UHFFFAOYSA-N 1,1-dimethoxy-1-(6-methoxynaphthalen-2-yl)propan-2-ol Chemical compound C1=C(C(OC)(OC)C(C)O)C=CC2=CC(OC)=CC=C21 GIFLQCVVIWXBBS-UHFFFAOYSA-N 0.000 description 5
XCOAABZEUNQHQG-UHFFFAOYSA-N 2-bromo-1-(6-methoxynaphthalen-2-yl)propan-1-one Chemical compound C1=C(C(=O)C(C)Br)C=CC2=CC(OC)=CC=C21 XCOAABZEUNQHQG-UHFFFAOYSA-N 0.000 description 5
239000012359 Methanesulfonyl chloride Substances 0.000 description 5
229910052786 argon Inorganic materials 0.000 description 5
125000003118 aryl group Chemical group 0.000 description 5
239000000463 material Substances 0.000 description 5
229910052751 metal Inorganic materials 0.000 description 5
239000002184 metal Substances 0.000 description 5
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 5
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 4
239000012230 colorless oil Substances 0.000 description 4
YUUFLSYPPSEURX-UHFFFAOYSA-N (2-phenyl-1,3-dioxolan-2-yl)methanol Chemical compound C=1C=CC=CC=1C1(CO)OCCO1 YUUFLSYPPSEURX-UHFFFAOYSA-N 0.000 description 3
ZUKRKSGRJOIXHQ-UHFFFAOYSA-N 1,1-dimethoxy-1-thiophen-2-ylpropan-2-ol Chemical compound COC(OC)(C(C)O)C1=CC=CS1 ZUKRKSGRJOIXHQ-UHFFFAOYSA-N 0.000 description 3
RQRBAXYLENGPSW-UHFFFAOYSA-N 1-(4-chlorophenyl)-1,1-dimethoxypropan-2-ol Chemical compound COC(OC)(C(C)O)C1=CC=C(Cl)C=C1 RQRBAXYLENGPSW-UHFFFAOYSA-N 0.000 description 3
QKHHCXOSPQAQQI-UHFFFAOYSA-N 2-bromo-1-(4-fluorophenyl)propan-1-one Chemical compound CC(Br)C(=O)C1=CC=C(F)C=C1 QKHHCXOSPQAQQI-UHFFFAOYSA-N 0.000 description 3
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
239000002841 Lewis acid Substances 0.000 description 3
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
125000002947 alkylene group Chemical group 0.000 description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
239000012043 crude product Substances 0.000 description 3
125000001475 halogen functional group Chemical group 0.000 description 3
150000007517 lewis acids Chemical class 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
230000007935 neutral effect Effects 0.000 description 3
239000003921 oil Substances 0.000 description 3
239000001301 oxygen Substances 0.000 description 3
229910052760 oxygen Inorganic materials 0.000 description 3
239000002798 polar solvent Substances 0.000 description 3
GTNZTNCLFRGDAO-UHFFFAOYSA-N 1,1-diethoxy-1-phenylpropan-2-ol Chemical compound CCOC(OCC)(C(C)O)C1=CC=CC=C1 GTNZTNCLFRGDAO-UHFFFAOYSA-N 0.000 description 2
KNQCPVANPIWTMP-UHFFFAOYSA-N 1,1-dimethoxy-1-(4-methoxyphenyl)-3-methylbutan-2-ol Chemical compound COC1=CC=C(C(OC)(OC)C(O)C(C)C)C=C1 KNQCPVANPIWTMP-UHFFFAOYSA-N 0.000 description 2
GHXKGEZOEBTGNZ-UHFFFAOYSA-N 1,1-dimethoxy-3,4-dihydro-2h-naphthalen-2-ol Chemical compound C1=CC=C2C(OC)(OC)C(O)CCC2=C1 GHXKGEZOEBTGNZ-UHFFFAOYSA-N 0.000 description 2
RBNLXKXUDXATPL-UHFFFAOYSA-N 1-(4-ethoxyphenyl)-1,1-dimethoxy-3-methylbutan-2-ol Chemical compound CCOC1=CC=C(C(OC)(OC)C(O)C(C)C)C=C1 RBNLXKXUDXATPL-UHFFFAOYSA-N 0.000 description 2
NRIKJIQJVPSYON-UHFFFAOYSA-N 1-[4-(difluoromethoxy)phenyl]-1,1-dimethoxy-3-methylbutan-2-ol Chemical compound CC(C)C(O)C(OC)(OC)C1=CC=C(OC(F)F)C=C1 NRIKJIQJVPSYON-UHFFFAOYSA-N 0.000 description 2
ISVYWKFEHBLNNY-UHFFFAOYSA-N 1-[4-(difluoromethoxy)phenyl]-1,1-dimethoxypropan-2-ol Chemical compound COC(OC)(C(C)O)C1=CC=C(OC(F)F)C=C1 ISVYWKFEHBLNNY-UHFFFAOYSA-N 0.000 description 2
XYHKNCXZYYTLRG-UHFFFAOYSA-N 1h-imidazole-2-carbaldehyde Chemical compound O=CC1=NC=CN1 XYHKNCXZYYTLRG-UHFFFAOYSA-N 0.000 description 2
SAKMPXRILWVZEG-UHFFFAOYSA-N 2-bromo-1-(4-chlorophenyl)propan-1-one Chemical compound CC(Br)C(=O)C1=CC=C(Cl)C=C1 SAKMPXRILWVZEG-UHFFFAOYSA-N 0.000 description 2
OHOJTVSVCZTMLJ-UHFFFAOYSA-N 2-bromo-1-(4-methoxyphenyl)-3-methylbutan-1-one Chemical compound COC1=CC=C(C(=O)C(Br)C(C)C)C=C1 OHOJTVSVCZTMLJ-UHFFFAOYSA-N 0.000 description 2
QNCDPGOJVGDTAN-UHFFFAOYSA-N 2-bromo-1-(4-methoxyphenyl)propan-1-one Chemical compound COC1=CC=C(C(=O)C(C)Br)C=C1 QNCDPGOJVGDTAN-UHFFFAOYSA-N 0.000 description 2
AYNCWMIFKFADCZ-UHFFFAOYSA-N 2-bromo-3,4-dihydro-2h-naphthalen-1-one Chemical compound C1=CC=C2C(=O)C(Br)CCC2=C1 AYNCWMIFKFADCZ-UHFFFAOYSA-N 0.000 description 2
GWYFCOCPABKNJV-UHFFFAOYSA-M 3-Methylbutanoic acid Natural products CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 description 2
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
239000005977 Ethylene Substances 0.000 description 2
229910021578 Iron(III) chloride Inorganic materials 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
125000004036 acetal group Chemical group 0.000 description 2
239000002253 acid Substances 0.000 description 2
229940121363 anti-inflammatory agent Drugs 0.000 description 2
239000002260 anti-inflammatory agent Substances 0.000 description 2
CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 2
GWYFCOCPABKNJV-UHFFFAOYSA-N beta-methyl-butyric acid Natural products CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 2
230000003197 catalytic effect Effects 0.000 description 2
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 2
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
239000011521 glass Substances 0.000 description 2
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 2
239000005457 ice water Substances 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
239000002917 insecticide Substances 0.000 description 2
RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
238000004811 liquid chromatography Methods 0.000 description 2
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
IZDROVVXIHRYMH-UHFFFAOYSA-N methanesulfonic anhydride Chemical compound CS(=O)(=O)OS(C)(=O)=O IZDROVVXIHRYMH-UHFFFAOYSA-N 0.000 description 2
FMHKJISHGRSNKW-UHFFFAOYSA-N n-[4-(2-hydroxy-1,1-dimethoxypropyl)phenyl]acetamide Chemical compound COC(OC)(C(C)O)C1=CC=C(NC(C)=O)C=C1 FMHKJISHGRSNKW-UHFFFAOYSA-N 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 2
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
239000011591 potassium Substances 0.000 description 2
SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
150000003512 tertiary amines Chemical class 0.000 description 2
WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 2
LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
PLGXEPHZCXBYLP-UHFFFAOYSA-N (-)-munitagine Chemical compound C1C2=CC=C(OC)C(O)=C2C2CC(C=C(C(=C3)O)OC)=C3C1N2C PLGXEPHZCXBYLP-UHFFFAOYSA-N 0.000 description 1
NRWSOBBGXZTHEW-UHFFFAOYSA-N (1,1-dimethoxy-1-phenylpropan-2-yl) 4-methylbenzenesulfonate Chemical compound C=1C=CC=CC=1C(OC)(OC)C(C)OS(=O)(=O)C1=CC=C(C)C=C1 NRWSOBBGXZTHEW-UHFFFAOYSA-N 0.000 description 1
RCMUSWVFAWGNOT-UHFFFAOYSA-N (1,1-dimethoxy-1-thiophen-2-ylpropan-2-yl) 4-methylbenzenesulfonate Chemical compound C=1C=CSC=1C(OC)(OC)C(C)OS(=O)(=O)C1=CC=C(C)C=C1 RCMUSWVFAWGNOT-UHFFFAOYSA-N 0.000 description 1
LGHDAAZKAQKNHF-UHFFFAOYSA-N (1,1-dimethoxy-1-thiophen-2-ylpropan-2-yl) benzenesulfonate Chemical compound C=1C=CSC=1C(OC)(OC)C(C)OS(=O)(=O)C1=CC=CC=C1 LGHDAAZKAQKNHF-UHFFFAOYSA-N 0.000 description 1
SYPZLTGWJSINKN-UHFFFAOYSA-N (1,1-dimethoxy-1-thiophen-2-ylpropan-2-yl) methanesulfonate Chemical compound CS(=O)(=O)OC(C)C(OC)(OC)C1=CC=CS1 SYPZLTGWJSINKN-UHFFFAOYSA-N 0.000 description 1
IDBUVBLEZSORQE-UHFFFAOYSA-N (1,1-dimethoxy-3,4-dihydro-2h-naphthalen-2-yl) methanesulfonate Chemical compound C1=CC=C2C(OC)(OC)C(OS(C)(=O)=O)CCC2=C1 IDBUVBLEZSORQE-UHFFFAOYSA-N 0.000 description 1
RJMIEHBSYVWVIN-LLVKDONJSA-N (2r)-2-[4-(3-oxo-1h-isoindol-2-yl)phenyl]propanoic acid Chemical compound C1=CC([C@H](C(O)=O)C)=CC=C1N1C(=O)C2=CC=CC=C2C1 RJMIEHBSYVWVIN-LLVKDONJSA-N 0.000 description 1
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MCABPPZJQISCCB-UHFFFAOYSA-N 1,1-dimethoxy-1-phenylpropan-2-ol Chemical compound COC(OC)(C(C)O)C1=CC=CC=C1 MCABPPZJQISCCB-UHFFFAOYSA-N 0.000 description 1
AHFMSNDOYCFEPH-UHFFFAOYSA-N 1,2-difluoroethane Chemical compound FCCF AHFMSNDOYCFEPH-UHFFFAOYSA-N 0.000 description 1
CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 1
YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
XZDQXUXIIGSDOM-UHFFFAOYSA-N 1-(4-fluorophenyl)-1,1-dimethoxypropan-2-ol Chemical compound COC(OC)(C(C)O)C1=CC=C(F)C=C1 XZDQXUXIIGSDOM-UHFFFAOYSA-N 0.000 description 1
DKGLLAZWGALJTQ-UHFFFAOYSA-N 1-[2-(4-methoxyphenyl)-1,3-dioxolan-2-yl]-2-methylpropan-1-ol Chemical compound C1=CC(OC)=CC=C1C1(C(O)C(C)C)OCCO1 DKGLLAZWGALJTQ-UHFFFAOYSA-N 0.000 description 1
JALUUBQFLPUJMY-UHFFFAOYSA-N 2-(4-phenylphenyl)propanoic acid Chemical compound C1=CC(C(C(O)=O)C)=CC=C1C1=CC=CC=C1 JALUUBQFLPUJMY-UHFFFAOYSA-N 0.000 description 1
CBUFJPKILKYIAA-UHFFFAOYSA-N 2-[4-(2-chloropropanoyl)phenyl]-3h-isoindol-1-one Chemical compound C1=CC(C(=O)C(Cl)C)=CC=C1N1C(=O)C2=CC=CC=C2C1 CBUFJPKILKYIAA-UHFFFAOYSA-N 0.000 description 1
PPMUQLSUMZXNFY-UHFFFAOYSA-N 2-[4-(2-hydroxy-1,1-dimethoxypropyl)phenyl]-3h-isoindol-1-one Chemical compound C1=CC(C(OC)(C(C)O)OC)=CC=C1N1C(=O)C2=CC=CC=C2C1 PPMUQLSUMZXNFY-UHFFFAOYSA-N 0.000 description 1
RMLXTCNQBBRUMO-UHFFFAOYSA-N 2-bromo-1-[4-(difluoromethoxy)phenyl]-3-methylbutan-1-one Chemical compound CC(C)C(Br)C(=O)C1=CC=C(OC(F)F)C=C1 RMLXTCNQBBRUMO-UHFFFAOYSA-N 0.000 description 1
WPDWOCRJBPXJFM-UHFFFAOYSA-N 2-bromo-1-phenylpropan-1-one Chemical compound CC(Br)C(=O)C1=CC=CC=C1 WPDWOCRJBPXJFM-UHFFFAOYSA-N 0.000 description 1
ISEXQXDJGISUKO-UHFFFAOYSA-N 2-bromo-1-thiophen-2-ylpropan-1-one Chemical compound CC(Br)C(=O)C1=CC=CS1 ISEXQXDJGISUKO-UHFFFAOYSA-N 0.000 description 1
GAIKZCUYADWIJQ-UHFFFAOYSA-N 2-methoxy-2-(4-methoxyphenyl)-3-methyloxirane Chemical compound C1=CC(OC)=CC=C1C1(OC)C(C)O1 GAIKZCUYADWIJQ-UHFFFAOYSA-N 0.000 description 1
KTKWUKAYWFMQSO-UHFFFAOYSA-N 2-thiophen-2-ylpropanoic acid Chemical compound OC(=O)C(C)C1=CC=CS1 KTKWUKAYWFMQSO-UHFFFAOYSA-N 0.000 description 1
KMMHZIBWCXYAAH-UHFFFAOYSA-N 4-bromobenzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=C(Br)C=C1 KMMHZIBWCXYAAH-UHFFFAOYSA-N 0.000 description 1
125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 1
125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
JXRGUPLJCCDGKG-UHFFFAOYSA-N 4-nitrobenzenesulfonyl chloride Chemical compound [O-][N+](=O)C1=CC=C(S(Cl)(=O)=O)C=C1 JXRGUPLJCCDGKG-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
229910015900 BF3 Inorganic materials 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
DCNKMFOPNDEDFU-UHFFFAOYSA-N CC(C)CCC(C(C1=CC=CC=C1)(OC)OC)OS(=O)(=O)C2=CC=CC=C2 Chemical compound CC(C)CCC(C(C1=CC=CC=C1)(OC)OC)OS(=O)(=O)C2=CC=CC=C2 DCNKMFOPNDEDFU-UHFFFAOYSA-N 0.000 description 1
XRAQCYTVWJAUMB-UHFFFAOYSA-N CCC(=O)C1=CC=C(C=C1)OS(=O)(=O)CC2=CC=CC=C2 Chemical compound CCC(=O)C1=CC=C(C=C1)OS(=O)(=O)CC2=CC=CC=C2 XRAQCYTVWJAUMB-UHFFFAOYSA-N 0.000 description 1
UQMFDGDYXQZHDM-UHFFFAOYSA-N COC(C(C(C)(C)C(C)(C)C)O)(C1=CC=CC=C1)OC Chemical compound COC(C(C(C)(C)C(C)(C)C)O)(C1=CC=CC=C1)OC UQMFDGDYXQZHDM-UHFFFAOYSA-N 0.000 description 1
LASBLBVGRMMTHL-UHFFFAOYSA-N COC(C(CCC(C)C)O)(C1=CC=CC=C1)OC Chemical compound COC(C(CCC(C)C)O)(C1=CC=CC=C1)OC LASBLBVGRMMTHL-UHFFFAOYSA-N 0.000 description 1
YVKNILSRQWPDMO-UHFFFAOYSA-N COC(CC(C)C)(C1=CC=CC=C1)OC Chemical compound COC(CC(C)C)(C1=CC=CC=C1)OC YVKNILSRQWPDMO-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
238000005727 Friedel-Crafts reaction Methods 0.000 description 1
101000585693 Homo sapiens Mitochondrial 2-oxodicarboxylate carrier Proteins 0.000 description 1
101001041245 Homo sapiens Ornithine decarboxylase Proteins 0.000 description 1
HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
CMWTZPSULFXXJA-UHFFFAOYSA-N Naproxen Natural products C1=C(C(C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-UHFFFAOYSA-N 0.000 description 1
102100021079 Ornithine decarboxylase Human genes 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
BGABKEVTHIJBIW-GMSGAONNSA-N [(1r,4s)-7,7-dimethyl-3-oxo-4-bicyclo[2.2.1]heptanyl]methanesulfonyl chloride Chemical compound C1C[C@@]2(CS(Cl)(=O)=O)C(=O)C[C@@H]1C2(C)C BGABKEVTHIJBIW-GMSGAONNSA-N 0.000 description 1
CSKHENBVWBJQPH-UHFFFAOYSA-N [1,1-dimethoxy-1-(4-methoxyphenyl)-3-methylbutan-2-yl] methanesulfonate Chemical compound COC1=CC=C(C(OC)(OC)C(OS(C)(=O)=O)C(C)C)C=C1 CSKHENBVWBJQPH-UHFFFAOYSA-N 0.000 description 1
YNMUTRIQYGWHPD-UHFFFAOYSA-N [1,1-dimethoxy-1-(4-methoxyphenyl)propan-2-yl] 4-methylbenzenesulfonate Chemical compound C1=CC(OC)=CC=C1C(OC)(OC)C(C)OS(=O)(=O)C1=CC=C(C)C=C1 YNMUTRIQYGWHPD-UHFFFAOYSA-N 0.000 description 1
UMLYYFJMAVUPPP-UHFFFAOYSA-N [1,1-dimethoxy-1-(4-methoxyphenyl)propan-2-yl] methanesulfonate Chemical compound COC1=CC=C(C(OC)(OC)C(C)OS(C)(=O)=O)C=C1 UMLYYFJMAVUPPP-UHFFFAOYSA-N 0.000 description 1
JHCIAVKSBSYOLH-UHFFFAOYSA-N [1,1-dimethoxy-1-(6-methoxynaphthalen-2-yl)propan-2-yl] 4-methylbenzenesulfonate Chemical compound C1=CC2=CC(OC)=CC=C2C=C1C(OC)(OC)C(C)OS(=O)(=O)C1=CC=C(C)C=C1 JHCIAVKSBSYOLH-UHFFFAOYSA-N 0.000 description 1
AJHDQRHCQVNBKI-UHFFFAOYSA-N [1,1-dimethoxy-1-(6-methoxynaphthalen-2-yl)propan-2-yl] benzenesulfonate Chemical compound C1=CC2=CC(OC)=CC=C2C=C1C(OC)(OC)C(C)OS(=O)(=O)C1=CC=CC=C1 AJHDQRHCQVNBKI-UHFFFAOYSA-N 0.000 description 1
BXHRAZVRNNAAHS-UHFFFAOYSA-N [1,1-dimethoxy-1-[4-(3-oxo-1h-isoindol-2-yl)phenyl]propan-2-yl] methanesulfonate Chemical compound C1=CC(C(OC)(C(C)OS(C)(=O)=O)OC)=CC=C1N1C(=O)C2=CC=CC=C2C1 BXHRAZVRNNAAHS-UHFFFAOYSA-N 0.000 description 1
PXDWPBVXONZSQW-UHFFFAOYSA-N [1-(4-acetamidophenyl)-1,1-dimethoxypropan-2-yl] methanesulfonate Chemical compound CS(=O)(=O)OC(C)C(OC)(OC)C1=CC=C(NC(C)=O)C=C1 PXDWPBVXONZSQW-UHFFFAOYSA-N 0.000 description 1
HSDMPRUKJUUKBV-UHFFFAOYSA-N [1-(4-chlorophenyl)-1,1-dimethoxypropan-2-yl] 4-methylbenzenesulfonate Chemical compound C=1C=C(Cl)C=CC=1C(OC)(OC)C(C)OS(=O)(=O)C1=CC=C(C)C=C1 HSDMPRUKJUUKBV-UHFFFAOYSA-N 0.000 description 1
IBWDSIJLKUANIP-UHFFFAOYSA-N [1-(4-ethoxyphenyl)-1,1-dimethoxy-3-methylbutan-2-yl] methanesulfonate Chemical compound CCOC1=CC=C(C(OC)(OC)C(OS(C)(=O)=O)C(C)C)C=C1 IBWDSIJLKUANIP-UHFFFAOYSA-N 0.000 description 1
KUYQEBCDDODNNP-UHFFFAOYSA-N [1-(4-fluorophenyl)-1,1-dimethoxypropan-2-yl] 4-methylbenzenesulfonate Chemical compound COC(C(C)OS(=O)(=O)C1=CC=C(C=C1)C)(C1=CC=C(C=C1)F)OC KUYQEBCDDODNNP-UHFFFAOYSA-N 0.000 description 1
HMBMCUXUJVZZNP-UHFFFAOYSA-N [1-(4-fluorophenyl)-1,1-dimethoxypropan-2-yl] methanesulfonate Chemical compound CS(=O)(=O)OC(C)C(OC)(OC)C1=CC=C(F)C=C1 HMBMCUXUJVZZNP-UHFFFAOYSA-N 0.000 description 1
OTLBDSOHYZVJBU-UHFFFAOYSA-N [1-[2-(4-methoxyphenyl)-1,3-dioxolan-2-yl]-2-methylpropyl] methanesulfonate Chemical compound C1=CC(OC)=CC=C1C1(C(OS(C)(=O)=O)C(C)C)OCCO1 OTLBDSOHYZVJBU-UHFFFAOYSA-N 0.000 description 1
LJEHJRLARFVHSX-UHFFFAOYSA-N [1-[4-(difluoromethoxy)phenyl]-1,1-dimethoxy-3-methylbutan-2-yl] methanesulfonate Chemical compound CS(=O)(=O)OC(C(C)C)C(OC)(OC)C1=CC=C(OC(F)F)C=C1 LJEHJRLARFVHSX-UHFFFAOYSA-N 0.000 description 1
QICGLPOQMNGMMP-UHFFFAOYSA-N [1-[4-(difluoromethoxy)phenyl]-1,1-dimethoxypropan-2-yl] methanesulfonate Chemical compound COC(C(C)OS(=O)(=O)C)(C1=CC=C(C=C1)OC(F)F)OC QICGLPOQMNGMMP-UHFFFAOYSA-N 0.000 description 1
PASACJUCYZVYOQ-UHFFFAOYSA-N [I].C[SiH](C)C Chemical compound [I].C[SiH](C)C PASACJUCYZVYOQ-UHFFFAOYSA-N 0.000 description 1
ZDPALFHDPFYJDY-UHFFFAOYSA-N [Na].OC=O Chemical compound [Na].OC=O ZDPALFHDPFYJDY-UHFFFAOYSA-N 0.000 description 1
238000006359 acetalization reaction Methods 0.000 description 1
150000001241 acetals Chemical group 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
229910000318 alkali metal phosphate Inorganic materials 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
239000002585 base Substances 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
239000004305 biphenyl Substances 0.000 description 1
235000010290 biphenyl Nutrition 0.000 description 1
238000009835 boiling Methods 0.000 description 1
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 1
WEDIIKBPDQQQJU-UHFFFAOYSA-N butane-1-sulfonyl chloride Chemical compound CCCCS(Cl)(=O)=O WEDIIKBPDQQQJU-UHFFFAOYSA-N 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
239000000920 calcium hydroxide Substances 0.000 description 1
229910001861 calcium hydroxide Inorganic materials 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000003814 drug Substances 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
238000000605 extraction Methods 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000003574 free electron Substances 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
125000001188 haloalkyl group Chemical group 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
125000002768 hydroxyalkyl group Chemical group 0.000 description 1
229960001680 ibuprofen Drugs 0.000 description 1
229960004187 indoprofen Drugs 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
HWSZZLVAJGOAAY-UHFFFAOYSA-L lead(II) chloride Chemical compound Cl[Pb]Cl HWSZZLVAJGOAAY-UHFFFAOYSA-L 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
239000001095 magnesium carbonate Substances 0.000 description 1
229910000021 magnesium carbonate Inorganic materials 0.000 description 1
VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
239000000347 magnesium hydroxide Substances 0.000 description 1
229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
238000002156 mixing Methods 0.000 description 1
FWBXOIYYUSIMST-UHFFFAOYSA-N n-[4-(2-chloropropanoyl)phenyl]acetamide Chemical compound CC(Cl)C(=O)C1=CC=C(NC(C)=O)C=C1 FWBXOIYYUSIMST-UHFFFAOYSA-N 0.000 description 1
DASJFYAPNPUBGG-UHFFFAOYSA-N naphthalene-1-sulfonyl chloride Chemical compound C1=CC=C2C(S(=O)(=O)Cl)=CC=CC2=C1 DASJFYAPNPUBGG-UHFFFAOYSA-N 0.000 description 1
229960002009 naproxen Drugs 0.000 description 1
CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical compound C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
229920000166 polytrimethylene carbonate Polymers 0.000 description 1
235000011056 potassium acetate Nutrition 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
229910000160 potassium phosphate Inorganic materials 0.000 description 1
235000011009 potassium phosphates Nutrition 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000001294 propane Substances 0.000 description 1
239000002728 pyrethroid Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
230000002000 scavenging effect Effects 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
239000001488 sodium phosphate Substances 0.000 description 1
229910000162 sodium phosphate Inorganic materials 0.000 description 1
JXKPEJDQGNYQSM-UHFFFAOYSA-M sodium propionate Chemical compound [Na+].CCC([O-])=O JXKPEJDQGNYQSM-UHFFFAOYSA-M 0.000 description 1
239000004324 sodium propionate Substances 0.000 description 1
235000010334 sodium propionate Nutrition 0.000 description 1
229960003212 sodium propionate Drugs 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
239000000725 suspension Substances 0.000 description 1
PUGUQINMNYINPK-UHFFFAOYSA-N tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(C(=O)CCl)CC1 PUGUQINMNYINPK-UHFFFAOYSA-N 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
125000004665 trialkylsilyl group Chemical group 0.000 description 1
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
PPLMQFARLJLZAO-UHFFFAOYSA-N triethyl(iodo)silane Chemical compound CC[Si](I)(CC)CC PPLMQFARLJLZAO-UHFFFAOYSA-N 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
GRGCWBWNLSTIEN-UHFFFAOYSA-N trifluoromethanesulfonyl chloride Chemical compound FC(F)(F)S(Cl)(=O)=O GRGCWBWNLSTIEN-UHFFFAOYSA-N 0.000 description 1
125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
SQQPOWPHFZZOEC-UHFFFAOYSA-N trimethylsilyl 1,1,2,2,2-pentafluoroethanesulfonate Chemical compound C[Si](C)(C)OS(=O)(=O)C(F)(F)C(F)(F)F SQQPOWPHFZZOEC-UHFFFAOYSA-N 0.000 description 1
FTVLMFQEYACZNP-UHFFFAOYSA-N trimethylsilyl trifluoromethanesulfonate Chemical compound C[Si](C)(C)OS(=O)(=O)C(F)(F)F FTVLMFQEYACZNP-UHFFFAOYSA-N 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1

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Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

HU843583A 1980-09-11 1981-09-09 Process for preparing alpha-sulphonyl-oxy- ketone-acetal derivatives HU192451B (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP55125355A JPS5750956A (en)	1980-09-11	1980-09-11	Alpha-sulfonyloxyalkanophenone acetal
JP55143042A JPS5767535A (en)	1980-10-15	1980-10-15	Preparation of alpha-aromatic group substituted alkanecarboxylic acid

Publications (1)

Publication Number	Publication Date
HU192451B true HU192451B (en)	1987-06-29

Family

ID=26461809

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
HU843583A HU192451B (en)	1980-09-11	1981-09-09	Process for preparing alpha-sulphonyl-oxy- ketone-acetal derivatives

Country Status (3)

Country	Link
AU (1)	AU549705B2 (cs)
CS (1)	CS255851B2 (cs)
HU (1)	HU192451B (cs)

1981
- 1981-09-07 AU AU75001/81A patent/AU549705B2/en not_active Ceased
- 1981-09-09 HU HU843583A patent/HU192451B/hu not_active IP Right Cessation
- 1981-09-11 CS CS673181A patent/CS255851B2/cs unknown

Also Published As

Publication number	Publication date
AU7500181A (en)	1982-03-18
CS255851B2 (en)	1988-03-15
AU549705B2 (en)	1986-02-06

Legal Events

Date	Code	Title	Description
1990-06-28	HU90	Patent valid on 900628
1994-06-28	HMM4	Cancellation of final prot. due to non-payment of fee

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