NO752739L - - Google Patents

Info

Publication number: NO752739L
Authority: NO; Norway
Prior art keywords: formula; compound; stated; methyl; mixture
Prior art date: 1974-08-06

Application number

NO752739A

Other languages

English (en)

Norwegian (no)

Inventor

S Wolfe

Original Assignee

Univ Kingston

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.)

1974-08-06

Filing date

1975-08-04

Publication date

1976-02-09

1974-08-06 Priority claimed from GB34614/74A external-priority patent/GB1510794A/en

1975-08-04 Application filed by Univ Kingston filed Critical Univ Kingston

1976-02-09 Publication of NO752739L publication Critical patent/NO752739L/no

Links

239000000203 mixture Substances 0.000 claims description 100
150000001875 compounds Chemical class 0.000 claims description 53
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 53
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 45
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 41
239000000460 chlorine Substances 0.000 claims description 41
238000000034 method Methods 0.000 claims description 31
-1 pivaloyloxy Chemical group 0.000 claims description 31
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 27
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 21
239000002904 solvent Substances 0.000 claims description 21
239000007858 starting material Substances 0.000 claims description 19
229910052739 hydrogen Inorganic materials 0.000 claims description 17
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 16
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 14
ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 claims description 13
125000000217 alkyl group Chemical group 0.000 claims description 12
238000007363 ring formation reaction Methods 0.000 claims description 12
BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims description 11
239000002253 acid Substances 0.000 claims description 10
239000001257 hydrogen Substances 0.000 claims description 10
238000011282 treatment Methods 0.000 claims description 10
239000011701 zinc Substances 0.000 claims description 9
229910052725 zinc Inorganic materials 0.000 claims description 9
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 8
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 8
150000001412 amines Chemical class 0.000 claims description 8
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
235000019253 formic acid Nutrition 0.000 claims description 8
125000005544 phthalimido group Chemical group 0.000 claims description 8
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 7
229910021626 Tin(II) chloride Inorganic materials 0.000 claims description 6
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
238000002844 melting Methods 0.000 claims description 6
230000008018 melting Effects 0.000 claims description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
235000011150 stannous chloride Nutrition 0.000 claims description 6
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
239000002841 Lewis acid Substances 0.000 claims description 5
229910052794 bromium Inorganic materials 0.000 claims description 5
229910052801 chlorine Inorganic materials 0.000 claims description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
150000007517 lewis acids Chemical class 0.000 claims description 5
125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 claims description 4
CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical group [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 4
238000005949 ozonolysis reaction Methods 0.000 claims description 4
150000003254 radicals Chemical class 0.000 claims description 4
230000008707 rearrangement Effects 0.000 claims description 4
TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 claims description 3
239000004593 Epoxy Substances 0.000 claims description 3
238000004090 dissolution Methods 0.000 claims description 3
230000026030 halogenation Effects 0.000 claims description 3
238000005658 halogenation reaction Methods 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
239000001119 stannous chloride Substances 0.000 claims description 3
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
239000004280 Sodium formate Substances 0.000 claims description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
XAKBSHICSHRJCL-UHFFFAOYSA-N [CH2]C(=O)C1=CC=CC=C1 Chemical group [CH2]C(=O)C1=CC=CC=C1 XAKBSHICSHRJCL-UHFFFAOYSA-N 0.000 claims description 2
125000004423 acyloxy group Chemical group 0.000 claims description 2
125000006307 alkoxy benzyl group Chemical group 0.000 claims description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
239000011737 fluorine Substances 0.000 claims description 2
229910052731 fluorine Inorganic materials 0.000 claims description 2
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
239000001301 oxygen Substances 0.000 claims description 2
229910052760 oxygen Inorganic materials 0.000 claims description 2
HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 claims description 2
235000019254 sodium formate Nutrition 0.000 claims description 2
229910052717 sulfur Chemical group 0.000 claims description 2
239000011593 sulfur Chemical group 0.000 claims description 2
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims 4
125000006007 trichloroethoxy group Chemical group 0.000 claims 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 2
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 2
208000032544 Cicatrix Diseases 0.000 claims 1
150000001298 alcohols Chemical class 0.000 claims 1
125000001246 bromo group Chemical group Br* 0.000 claims 1
238000000354 decomposition reaction Methods 0.000 claims 1
231100000241 scar Toxicity 0.000 claims 1
230000037387 scars Effects 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 84
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 72
239000000243 solution Substances 0.000 description 54
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 51
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 30
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 30
238000006243 chemical reaction Methods 0.000 description 29
239000006260 foam Substances 0.000 description 27
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 24
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
239000003208 petroleum Substances 0.000 description 21
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 16
239000000463 material Substances 0.000 description 16
239000000741 silica gel Substances 0.000 description 16
229910002027 silica gel Inorganic materials 0.000 description 16
229960000583 acetic acid Drugs 0.000 description 15
238000001704 evaporation Methods 0.000 description 14
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 13
230000008020 evaporation Effects 0.000 description 12
239000000047 product Substances 0.000 description 12
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 12
238000002474 experimental method Methods 0.000 description 11
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
239000000284 extract Substances 0.000 description 10
239000000543 intermediate Substances 0.000 description 10
150000002596 lactones Chemical class 0.000 description 10
230000002829 reductive effect Effects 0.000 description 10
HUHXLHLWASNVDB-UHFFFAOYSA-N 2-(oxan-2-yloxy)oxane Chemical compound O1CCCCC1OC1OCCCC1 HUHXLHLWASNVDB-UHFFFAOYSA-N 0.000 description 9
239000012267 brine Substances 0.000 description 9
239000011541 reaction mixture Substances 0.000 description 9
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 9
JXQGXEUVZKGSDW-UHFFFAOYSA-N O=C1C[ClH]N1 Chemical compound O=C1C[ClH]N1 JXQGXEUVZKGSDW-UHFFFAOYSA-N 0.000 description 8
MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical class O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 description 8
238000007256 debromination reaction Methods 0.000 description 8
238000002955 isolation Methods 0.000 description 8
239000010410 layer Substances 0.000 description 8
238000001035 drying Methods 0.000 description 7
239000012362 glacial acetic acid Substances 0.000 description 7
150000002924 oxiranes Chemical class 0.000 description 7
238000002360 preparation method Methods 0.000 description 7
239000011780 sodium chloride Substances 0.000 description 7
AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 7
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 6
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
230000031709 bromination Effects 0.000 description 6
238000005893 bromination reaction Methods 0.000 description 6
238000001914 filtration Methods 0.000 description 6
150000004675 formic acid derivatives Chemical class 0.000 description 6
239000005457 ice water Substances 0.000 description 6
239000012044 organic layer Substances 0.000 description 6
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
238000003756 stirring Methods 0.000 description 6
XYPISWUKQGWYGX-UHFFFAOYSA-N 2,2,2-trifluoroethaneperoxoic acid Chemical compound OOC(=O)C(F)(F)F XYPISWUKQGWYGX-UHFFFAOYSA-N 0.000 description 5
239000008346 aqueous phase Substances 0.000 description 5
125000004429 atom Chemical group 0.000 description 5
238000004587 chromatography analysis Methods 0.000 description 5
238000010586 diagram Methods 0.000 description 5
150000002148 esters Chemical class 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
238000001953 recrystallisation Methods 0.000 description 5
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
150000001649 bromium compounds Chemical group 0.000 description 4
238000001816 cooling Methods 0.000 description 4
238000010828 elution Methods 0.000 description 4
238000005755 formation reaction Methods 0.000 description 4
239000007789 gas Substances 0.000 description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
ZUSUVEKHEZURSD-UHFFFAOYSA-N oct-5-enal Chemical compound CCC=CCCCC=O ZUSUVEKHEZURSD-UHFFFAOYSA-N 0.000 description 4
238000010992 reflux Methods 0.000 description 4
239000011734 sodium Substances 0.000 description 4
KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
150000001336 alkenes Chemical class 0.000 description 3
125000002393 azetidinyl group Chemical group 0.000 description 3
BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 3
238000006073 displacement reaction Methods 0.000 description 3
150000002085 enols Chemical class 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
238000005406 washing Methods 0.000 description 3
FMCAFXHLMUOIGG-IWFBPKFRSA-N (2s)-2-[[(2s)-2-[[(2s)-2-[[(2r)-2-formamido-3-sulfanylpropanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxy-2,5-dimethylphenyl)propanoyl]amino]-4-methylsulfanylbutanoic acid Chemical compound O=CN[C@@H](CS)C(=O)N[C@@H](C(C)C)C(=O)N[C@H](C(=O)N[C@@H](CCSC)C(O)=O)CC1=CC(C)=C(O)C=C1C FMCAFXHLMUOIGG-IWFBPKFRSA-N 0.000 description 2
QXNSHVVNEOAAOF-RXMQYKEDSA-N (6R)-4-oxa-5-thia-1-azabicyclo[4.2.0]oct-2-en-8-one Chemical class S1OC=CN2[C@H]1CC2=O QXNSHVVNEOAAOF-RXMQYKEDSA-N 0.000 description 2
WPVIUZQMFSKPMN-UHFFFAOYSA-N 1-hydroxyazetidin-2-one Chemical class ON1CCC1=O WPVIUZQMFSKPMN-UHFFFAOYSA-N 0.000 description 2
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
239000004342 Benzoyl peroxide Substances 0.000 description 2
OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
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 2
230000009102 absorption Effects 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
239000006286 aqueous extract Substances 0.000 description 2
235000019400 benzoyl peroxide Nutrition 0.000 description 2
235000011089 carbon dioxide Nutrition 0.000 description 2
MOIPGXQKZSZOQX-UHFFFAOYSA-N carbonyl bromide Chemical compound BrC(Br)=O MOIPGXQKZSZOQX-UHFFFAOYSA-N 0.000 description 2
QILSFLSDHQAZET-UHFFFAOYSA-N diphenylmethanol Chemical compound C=1C=CC=CC=1C(O)C1=CC=CC=C1 QILSFLSDHQAZET-UHFFFAOYSA-N 0.000 description 2
238000006345 epimerization reaction Methods 0.000 description 2
239000004744 fabric Substances 0.000 description 2
239000002198 insoluble material Substances 0.000 description 2
239000008188 pellet Substances 0.000 description 2
150000004965 peroxy acids Chemical class 0.000 description 2
238000000746 purification Methods 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
239000012266 salt solution Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
229960002317 succinimide Drugs 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
ZUBXPSDFPQTKQN-ZCFIWIBFSA-N (6r)-3-hydroxy-5-thia-1-azabicyclo[4.2.0]oct-2-en-8-one Chemical class S1CC(O)=CN2C(=O)C[C@H]21 ZUBXPSDFPQTKQN-ZCFIWIBFSA-N 0.000 description 1
FMZQBJUJTDAWOW-UHFFFAOYSA-N 2-bromo-3-oxobutanoic acid Chemical compound CC(=O)C(Br)C(O)=O FMZQBJUJTDAWOW-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
101100283604 Caenorhabditis elegans pigk-1 gene Proteins 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
FIWILGQIZHDAQG-UHFFFAOYSA-N NC1=C(C(=O)NCC2=CC=C(C=C2)OCC(F)(F)F)C=C(C(=N1)N)N1N=C(N=C1)C1(CC1)C(F)(F)F Chemical compound NC1=C(C(=O)NCC2=CC=C(C=C2)OCC(F)(F)F)C=C(C(=N1)N)N1N=C(N=C1)C1(CC1)C(F)(F)F FIWILGQIZHDAQG-UHFFFAOYSA-N 0.000 description 1
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
ITLHXEGAYQFOHJ-UHFFFAOYSA-N [diazo(phenyl)methyl]benzene Chemical compound C=1C=CC=CC=1C(=[N+]=[N-])C1=CC=CC=C1 ITLHXEGAYQFOHJ-UHFFFAOYSA-N 0.000 description 1
WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 description 1
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
229940092714 benzenesulfonic acid Drugs 0.000 description 1
230000000903 blocking effect Effects 0.000 description 1
239000000872 buffer Substances 0.000 description 1
239000006172 buffering agent Substances 0.000 description 1
BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
239000000292 calcium oxide Substances 0.000 description 1
ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000005660 chlorination reaction Methods 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
OQNGCCWBHLEQFN-UHFFFAOYSA-N chloroform;hexane Chemical compound ClC(Cl)Cl.CCCCCC OQNGCCWBHLEQFN-UHFFFAOYSA-N 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
NPOMSUOUAZCMBL-UHFFFAOYSA-N dichloromethane;ethoxyethane Chemical compound ClCCl.CCOCC NPOMSUOUAZCMBL-UHFFFAOYSA-N 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
238000007865 diluting Methods 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000006735 epoxidation reaction Methods 0.000 description 1
229920006334 epoxy coating Polymers 0.000 description 1
238000000605 extraction Methods 0.000 description 1
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
238000007306 functionalization reaction Methods 0.000 description 1
239000011521 glass Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical group C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
230000026045 iodination Effects 0.000 description 1
238000006192 iodination reaction Methods 0.000 description 1
125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
150000003951 lactams Chemical group 0.000 description 1
239000011968 lewis acid catalyst Substances 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
238000006140 methanolysis reaction Methods 0.000 description 1
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical class [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000010502 orange oil Substances 0.000 description 1
125000001477 organic nitrogen group Chemical group 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
WURFKUQACINBSI-UHFFFAOYSA-M ozonide Chemical compound [O]O[O-] WURFKUQACINBSI-UHFFFAOYSA-M 0.000 description 1
229940049954 penicillin Drugs 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
238000011084 recovery Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
238000006748 scratching Methods 0.000 description 1
230000002393 scratching effect Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000002195 soluble material Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000000758 substrate Substances 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
239000000725 suspension Substances 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
YMBCJWGVCUEGHA-UHFFFAOYSA-M tetraethylammonium chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC YMBCJWGVCUEGHA-UHFFFAOYSA-M 0.000 description 1
CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical compound C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 description 1
150000007970 thio esters Chemical class 0.000 description 1
230000009466 transformation Effects 0.000 description 1
229960002415 trichloroethylene Drugs 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1

Landscapes

Plural Heterocyclic Compounds (AREA)

NO752739A 1974-08-06 1975-08-04 NO752739L (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB34614/74A GB1510794A (en)	1974-08-06	1974-08-06	1-oxacephems and intermediates therefor
GB3461475		1975-06-30

Publications (1)

Publication Number	Publication Date
NO752739L true NO752739L (fr)	1976-02-09

Family

ID=26262361

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO752739A NO752739L (fr)	1974-08-06	1975-08-04

Country Status (1)

Country	Link
NO (1)	NO752739L (fr)

1975
- 1975-08-04 NO NO752739A patent/NO752739L/no unknown

Publication	Publication Date	Title
US4013653A (en)	1977-03-22	1-oxacephems
CZ300859B6 (cs)	2009-08-26	Zpusob prípravy alkalické soli volného hydrofobního sulfonamidového derivátu
NO173016B (no)	1993-07-05	Analogifremgangsmaate ved fremstilling av terapeutisk aktive beta-laktamderivater
NO172577B (no)	1993-05-03	Fremgangsmaate og mellomprodukter ved fremstilling av substituerte indolinonderivater
NO162343B (no)	1989-09-04	7-acylamino-1-detia-1-oksacefamforbindelser egnet som mellomprodukt for fremstilling av 7beta-acylamino-1-detia-1-oksacefalosporiner.
JPS61238758A (ja)	1986-10-24	エピポドフイロトキシンおよび関連化合物を製造する中間体並びにその製造および使用方法
NO752739L (fr)	1976-02-09
NO149352B (no)	1983-12-27	Azetidinonderivater for anvendelse som mellomprodukt ved fremstilling av farmakologisk aktive oksadetiacefalosporiner
US4200571A (en)	1980-04-29	4-Chloroazetidinone
NO159658B (no)	1988-10-17	Mellomprodukt for fremstilling av 1,1-diokso-penicillanoyloksymetyl-6-(2-amino-2-fenyl-acetamido)penicillanat-antibiotika.
SU1039444A3 (ru)	1983-08-30	Способ получени 1-оксадетиацефалоспоринов
SU659088A3 (ru)	1979-04-25	Способ получени гетероциклических соединений
US4581173A (en)	1986-04-08	Production of hydroxymethylbutenoic acids via oxidation
Lera et al.	2001	Azatriquinanes. Part 4. 1 The chemistry of azatriquinenamine and its bromination products
JP3151074B2 (ja)	2001-04-03	１Ｒ，ｃｉｓ−２，２−ジメチル−３−ホルミルシクロプロパン−１−カルボン酸のラクトンの新製造法及びハロゲン化中間体
BE897064A (fr)	1983-10-17	Procede de preparation de composes de 3-methylene cepham
KR100245059B1 (ko)	2000-03-02	1r, 시스2, 2-디메틸-3-포르밀-시클로프로판-1-카르복실산의 락톤의 신규 제조 방법 및 중간체
SU453832A3 (ru)	1974-12-15	СПОСОБ ПОЛУЧЕНИЯ ГАЛОГЕНСТЕРОИДОВ ПРЕГНАНОВОГО РЯДА1Изобретение относитс к способу иолучени новых галогенстероидов прегнанового р да, содержащи.х двойные св зи в положени .х 4 и 6 и обладающих высокой физиологической активностью.5Известен сиособ получени галогенстероидов воздействием галогенводорода на соответствующий эпоксистероид, с иоследующей дегидратацией образовавщегос галоидгидрина. ю Примеиив этот сиособ, авторы получили ио- вые галогенстероиды ирегнанового р да, обладающие ценными свойствами.Предлагаемый сиособ получени галогеи- 15 стероидов прегианового р да формулы I\=2t L•Огде Z — два алифатических, ароматических или аралифатических углеводородных остатка, или группа ~.C==Z— циклоалкилидеиова / /группа и X — атом фтора или хлора, заключаетс в том, что в соединении формулы II' dH.FCHoF20где RI и Rj каждый — свободна или этери- ф:1щирова'Н«а в сложный -или в простой эфир оксигруипа или Ri вместе с R2 — груипа2530где RI и R2 имеют указанные значени , расщепл ют эпоксидное кольцо действием гало- геиводорода НХ, где X имеет указанное значение, или при помощи агента, выдел ющего этот галогеиводород, и получаемый галоген- гндрин, одновременно или последовательно дегидратируют обработкой галоген водородной кнслотой.
US3703530A (en)	1972-11-21	Alkyl - 2 - alkyl - 2,3 - dicarboxy-5-norbornene - 7-acetate intermediates for the total synthesis of elenolic acids and analogs thereof
Morita et al.	2001	An Efficient Preparation of 2H-Cyclohepta (b) furan-2-ones
SU1176842A3 (ru)	1985-08-30	Способ получени 1,4:3,6-диангидро-2,5-диазидо-2,5-дидеокси- @ -маннита
De Buyck et al.	1988	Hexachlorodimedone: Ring opening and intramolecular substitution of halogen. Preparation of γ, δ‐Diketoacids and Esters
US3793346A (en)	1974-02-19	Intermediate in the total synthesis of elenolic acid
JPH05221947A (ja)	1993-08-31	シクロプロパン誘導体の製法
DK145598B (da)	1982-12-20	Fremgangsmaade til fremstilling af cephalosporinsulfoxydforbindelser