NL1012865C2 - 1-Fenyl-3-oxopropaan-1-sulfonzuren en -sulfonaten en zuivere enantiomeren daarvan. - Google Patents

1-Fenyl-3-oxopropaan-1-sulfonzuren en -sulfonaten en zuivere enantiomeren daarvan. Download PDF

Info

Publication number: NL1012865C2
Authority: NL; Netherlands
Prior art keywords: sulfonic acid; groups; oxopropane; group; phenyl
Prior art date: 1999-08-19

Application number

NL1012865A

Other languages

English (en)

Dutch (nl)

Inventor

Hans Wijnberg

Kees Pouwer

Josu Nieuwenhuijzen

Ton Renu Vries

Original Assignee

Dsm Nv

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.)

1999-08-19

Filing date

1999-08-19

Publication date

2001-02-20

1999-08-19 Application filed by Dsm Nv filed Critical Dsm Nv

1999-08-19 Priority to NL1012865A priority Critical patent/NL1012865C2/nl

2000-08-18 Priority to AU66010/00A priority patent/AU6601000A/en

2000-08-18 Priority to DE60015353T priority patent/DE60015353D1/de

2000-08-18 Priority to JP2001518417A priority patent/JP2003507452A/ja

2000-08-18 Priority to AT00953585T priority patent/ATE280755T1/de

2000-08-18 Priority to PCT/NL2000/000577 priority patent/WO2001014327A1/en

2000-08-18 Priority to EP20000953585 priority patent/EP1204636B1/de

2000-08-18 Priority to US10/069,167 priority patent/US6639103B1/en

2001-02-20 Application granted granted Critical

2001-02-20 Publication of NL1012865C2 publication Critical patent/NL1012865C2/nl

Links

HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 title claims abstract description 39
150000003871 sulfonates Chemical class 0.000 title abstract description 8
RIPOBGAKZCUNGE-UHFFFAOYSA-N 3-oxo-1-phenylpropane-1-sulfonic acid Chemical class O=CCC(S(=O)(=O)O)C1=CC=CC=C1 RIPOBGAKZCUNGE-UHFFFAOYSA-N 0.000 title description 6
150000001875 compounds Chemical class 0.000 claims abstract description 69
239000000203 mixture Substances 0.000 claims abstract description 48
-1 1,3-disubstituted-3-oxopropane-1-sulfonic acids Chemical class 0.000 claims abstract description 8
150000003839 salts Chemical class 0.000 claims description 50
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 48
125000003545 alkoxy group Chemical group 0.000 claims description 21
239000003795 chemical substances by application Substances 0.000 claims description 20
125000000753 cycloalkyl group Chemical group 0.000 claims description 20
125000000000 cycloalkoxy group Chemical group 0.000 claims description 19
125000000217 alkyl group Chemical group 0.000 claims description 17
238000000034 method Methods 0.000 claims description 16
125000003118 aryl group Chemical group 0.000 claims description 14
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
125000003396 thiol group Chemical group [H]S* 0.000 claims description 14
150000003460 sulfonic acids Chemical class 0.000 claims description 13
125000003710 aryl alkyl group Chemical group 0.000 claims description 12
125000005843 halogen group Chemical group 0.000 claims description 12
125000002252 acyl group Chemical group 0.000 claims description 10
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 9
125000002560 nitrile group Chemical group 0.000 claims description 9
125000003277 amino group Chemical group 0.000 claims description 8
229910052708 sodium Inorganic materials 0.000 claims description 8
239000011734 sodium Substances 0.000 claims description 8
125000000101 thioether group Chemical group 0.000 claims description 8
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 claims description 7
150000001412 amines Chemical class 0.000 claims description 7
238000004519 manufacturing process Methods 0.000 claims description 7
125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 6
229910052783 alkali metal Inorganic materials 0.000 claims description 6
150000001340 alkali metals Chemical class 0.000 claims description 6
125000002877 alkyl aryl group Chemical group 0.000 claims description 6
150000001413 amino acids Chemical class 0.000 claims description 6
239000002904 solvent Substances 0.000 claims description 6
150000001414 amino alcohols Chemical class 0.000 claims description 5
125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 5
125000001072 heteroaryl group Chemical group 0.000 claims description 5
AZEJJUXBTGABIB-UHFFFAOYSA-M sodium;3-(4-chlorophenyl)-3-oxo-1-pyridin-2-ylpropane-1-sulfonate Chemical compound [Na+].C=1C=CC=NC=1C(S(=O)(=O)[O-])CC(=O)C1=CC=C(Cl)C=C1 AZEJJUXBTGABIB-UHFFFAOYSA-M 0.000 claims description 5
OXEUAMCPORMBOK-UHFFFAOYSA-M sodium;3-(4-chlorophenyl)-3-oxo-1-pyridin-4-ylpropane-1-sulfonate Chemical compound [Na+].C=1C=NC=CC=1C(S(=O)(=O)[O-])CC(=O)C1=CC=C(Cl)C=C1 OXEUAMCPORMBOK-UHFFFAOYSA-M 0.000 claims description 5
MMEONIXEUXAJON-UHFFFAOYSA-M sodium;3-(4-methoxyphenyl)-3-oxo-1-pyridin-4-ylpropane-1-sulfonate Chemical compound [Na+].C1=CC(OC)=CC=C1C(=O)CC(S([O-])(=O)=O)C1=CC=NC=C1 MMEONIXEUXAJON-UHFFFAOYSA-M 0.000 claims description 5
GCBADYUQQAEZBW-UHFFFAOYSA-N 3-oxo-1,3-diphenylpropane-1-sulfonic acid Chemical compound C=1C=CC=CC=1C(S(=O)(=O)O)CC(=O)C1=CC=CC=C1 GCBADYUQQAEZBW-UHFFFAOYSA-N 0.000 claims description 4
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 4
150000001342 alkaline earth metals Chemical class 0.000 claims description 4
125000005213 alkyl heteroaryl group Chemical group 0.000 claims description 4
239000000460 chlorine Substances 0.000 claims description 4
125000004446 heteroarylalkyl group Chemical group 0.000 claims description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
OVRIRADLDDDMRZ-UHFFFAOYSA-M sodium;3-(2-hydroxy-3-methoxy-5-methylphenyl)-3-oxo-1-phenylpropane-1-sulfonate Chemical compound [Na+].COC1=CC(C)=CC(C(=O)CC(C=2C=CC=CC=2)S([O-])(=O)=O)=C1O OVRIRADLDDDMRZ-UHFFFAOYSA-M 0.000 claims description 4
LOVCIMUFNSEVIW-UHFFFAOYSA-M sodium;3-(4-chlorophenyl)-3-oxo-1-pyridin-3-ylpropane-1-sulfonate Chemical compound [Na+].C=1C=CN=CC=1C(S(=O)(=O)[O-])CC(=O)C1=CC=C(Cl)C=C1 LOVCIMUFNSEVIW-UHFFFAOYSA-M 0.000 claims description 4
XWLADUYOCFSSQD-UHFFFAOYSA-M sodium;3-oxo-1,3-diphenylpropane-1-sulfonate Chemical compound [Na+].C=1C=CC=CC=1C(S(=O)(=O)[O-])CC(=O)C1=CC=CC=C1 XWLADUYOCFSSQD-UHFFFAOYSA-M 0.000 claims description 4
AWWSTZRJKXYUIX-UHFFFAOYSA-N 1-(3,4-dimethoxyphenyl)-3-(4-hydroxy-3-methoxyphenyl)-3-oxopropane-1-sulfonic acid Chemical compound C1=C(O)C(OC)=CC(C(=O)CC(C=2C=C(OC)C(OC)=CC=2)S(O)(=O)=O)=C1 AWWSTZRJKXYUIX-UHFFFAOYSA-N 0.000 claims description 3
OGFYWWJENJJMGM-UHFFFAOYSA-N 1-(4-hydroxy-3-methoxyphenyl)-3-(2-hydroxyphenyl)-3-oxopropane-1-sulfonic acid Chemical compound C1=C(O)C(OC)=CC(C(CC(=O)C=2C(=CC=CC=2)O)S(O)(=O)=O)=C1 OGFYWWJENJJMGM-UHFFFAOYSA-N 0.000 claims description 3
NPAHGHRTJLMYAK-UHFFFAOYSA-N 1-(4-methoxyphenyl)-3-oxo-3-phenylpropane-1-sulfonic acid Chemical compound C1=CC(OC)=CC=C1C(S(O)(=O)=O)CC(=O)C1=CC=CC=C1 NPAHGHRTJLMYAK-UHFFFAOYSA-N 0.000 claims description 3
PFEKVFHXECPGJO-UHFFFAOYSA-N 1-(4-methylphenyl)-3-oxo-3-phenylpropane-1-sulfonic acid Chemical compound C1=CC(C)=CC=C1C(S(O)(=O)=O)CC(=O)C1=CC=CC=C1 PFEKVFHXECPGJO-UHFFFAOYSA-N 0.000 claims description 3
JTEURNIHEPFUIJ-UHFFFAOYSA-N 2-amino-2-(4-methylphenyl)ethanol Chemical group CC1=CC=C(C(N)CO)C=C1 JTEURNIHEPFUIJ-UHFFFAOYSA-N 0.000 claims description 3
QFWFBYDGKJAGAU-UHFFFAOYSA-N 3-(2-hydroxyphenyl)-3-oxo-1-phenylpropane-1-sulfonic acid Chemical compound OC1=CC=CC=C1C(=O)CC(S(O)(=O)=O)C1=CC=CC=C1 QFWFBYDGKJAGAU-UHFFFAOYSA-N 0.000 claims description 3
AJHWDFUBSWYPER-UHFFFAOYSA-N 3-(4-hydroxy-3-methoxyphenyl)-3-oxo-1-phenylpropane-1-sulfonic acid Chemical compound C1=C(O)C(OC)=CC(C(=O)CC(C=2C=CC=CC=2)S(O)(=O)=O)=C1 AJHWDFUBSWYPER-UHFFFAOYSA-N 0.000 claims description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
DQFBYFPFKXHELB-UHFFFAOYSA-N Chalcone Natural products C=1C=CC=CC=1C(=O)C=CC1=CC=CC=C1 DQFBYFPFKXHELB-UHFFFAOYSA-N 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 3
VWHSHVOMWXHQBN-UHFFFAOYSA-N 1-(4-fluorophenyl)-3-oxo-3-phenylpropane-1-sulfonic acid Chemical compound C=1C=C(F)C=CC=1C(S(=O)(=O)O)CC(=O)C1=CC=CC=C1 VWHSHVOMWXHQBN-UHFFFAOYSA-N 0.000 claims description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
229910052700 potassium Chemical group 0.000 claims description 2
239000011591 potassium Chemical group 0.000 claims description 2
239000003341 Bronsted base Substances 0.000 claims 5
125000004104 aryloxy group Chemical group 0.000 claims 4
HOYCBKZPDXKDFF-UHFFFAOYSA-N 3-(4-bromophenyl)-3-oxo-1-phenylpropane-1-sulfonic acid Chemical compound C=1C=CC=CC=1C(S(=O)(=O)O)CC(=O)C1=CC=C(Br)C=C1 HOYCBKZPDXKDFF-UHFFFAOYSA-N 0.000 claims 2
VSTMHDICBUWUPQ-UHFFFAOYSA-N 3-(4-chlorophenyl)-3-oxo-1-phenylpropane-1-sulfonic acid Chemical compound C=1C=CC=CC=1C(S(=O)(=O)O)CC(=O)C1=CC=C(Cl)C=C1 VSTMHDICBUWUPQ-UHFFFAOYSA-N 0.000 claims 2
125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims 2
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 2
QMHDTKUBDZUMNH-IZZDOVSWSA-N (e)-1-(4-bromophenyl)-3-phenylprop-2-en-1-one Chemical compound C1=CC(Br)=CC=C1C(=O)\C=C\C1=CC=CC=C1 QMHDTKUBDZUMNH-IZZDOVSWSA-N 0.000 claims 1
HIINIOLNGCQCSM-IZZDOVSWSA-N (e)-1-(4-chlorophenyl)-3-phenylprop-2-en-1-one Chemical compound C1=CC(Cl)=CC=C1C(=O)\C=C\C1=CC=CC=C1 HIINIOLNGCQCSM-IZZDOVSWSA-N 0.000 claims 1
XNLFHCPVTULKIV-VAWYXSNFSA-N (e)-3-(4-methylphenyl)-1-phenylprop-2-en-1-one Chemical compound C1=CC(C)=CC=C1\C=C\C(=O)C1=CC=CC=C1 XNLFHCPVTULKIV-VAWYXSNFSA-N 0.000 claims 1
PJQPMVOTTQEVKG-UHFFFAOYSA-N 3-(2-hydroxy-3-methoxy-5-methylphenyl)-3-oxo-1-phenylpropane-1-sulfonic acid Chemical compound COC1=CC(C)=CC(C(=O)CC(C=2C=CC=CC=2)S(O)(=O)=O)=C1O PJQPMVOTTQEVKG-UHFFFAOYSA-N 0.000 claims 1
XUFXKBJMCRJATM-UHFFFAOYSA-N 3-(4-methoxyphenyl)-1-phenylprop-2-en-1-one Chemical compound C1=CC(OC)=CC=C1C=CC(=O)C1=CC=CC=C1 XUFXKBJMCRJATM-UHFFFAOYSA-N 0.000 claims 1
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 claims 1
150000007530 organic bases Chemical class 0.000 claims 1
DQFBYFPFKXHELB-VAWYXSNFSA-N trans-chalcone Chemical compound C=1C=CC=CC=1C(=O)\C=C\C1=CC=CC=C1 DQFBYFPFKXHELB-VAWYXSNFSA-N 0.000 claims 1
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 36
238000005481 NMR spectroscopy Methods 0.000 description 12
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
125000004169 (C1-C6) alkyl group Chemical group 0.000 description 7
238000005160 1H NMR spectroscopy Methods 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
239000000243 solution Substances 0.000 description 5
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
238000003776 cleavage reaction Methods 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
238000010992 reflux Methods 0.000 description 4
230000007017 scission Effects 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000002585 base Substances 0.000 description 3
239000012044 organic layer Substances 0.000 description 3
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 3
238000003756 stirring Methods 0.000 description 3
KUIZKZHDMPERHR-UHFFFAOYSA-N 1-phenylprop-2-en-1-one Chemical compound C=CC(=O)C1=CC=CC=C1 KUIZKZHDMPERHR-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 2
239000002253 acid Substances 0.000 description 2
125000004429 atom Chemical group 0.000 description 2
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
244000309464 bull Species 0.000 description 2
150000001789 chalcones Chemical class 0.000 description 2
235000005513 chalcones Nutrition 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
239000010410 layer Substances 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
229910021645 metal ion Inorganic materials 0.000 description 2
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
SDZKEWVGMOFZPU-UHFFFAOYSA-M sodium;3-(2-hydroxyphenyl)-3-oxo-1-phenylpropane-1-sulfonate Chemical compound [Na+].OC1=CC=CC=C1C(=O)CC(S([O-])(=O)=O)C1=CC=CC=C1 SDZKEWVGMOFZPU-UHFFFAOYSA-M 0.000 description 2
FQZWSVJBZBOSLN-UHFFFAOYSA-M sodium;3-(4-hydroxy-3-methoxyphenyl)-3-oxo-1-phenylpropane-1-sulfonate Chemical compound [Na+].C1=C(O)C(OC)=CC(C(=O)CC(C=2C=CC=CC=2)S([O-])(=O)=O)=C1 FQZWSVJBZBOSLN-UHFFFAOYSA-M 0.000 description 2
239000007787 solid Substances 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
RSPCKAHMRANGJZ-UHFFFAOYSA-N thiohydroxylamine Chemical compound SN RSPCKAHMRANGJZ-UHFFFAOYSA-N 0.000 description 2
ONDSBJMLAHVLMI-UHFFFAOYSA-N trimethylsilyldiazomethane Chemical compound C[Si](C)(C)[CH-][N+]#N ONDSBJMLAHVLMI-UHFFFAOYSA-N 0.000 description 2
238000003828 vacuum filtration Methods 0.000 description 2
JTEURNIHEPFUIJ-VIFPVBQESA-N (2r)-2-amino-2-(4-methylphenyl)ethanol Chemical compound CC1=CC=C([C@@H](N)CO)C=C1 JTEURNIHEPFUIJ-VIFPVBQESA-N 0.000 description 1
125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 1
MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
COFMBBYARPOGBA-UHFFFAOYSA-N 1-phenylethanesulfonic acid Chemical compound OS(=O)(=O)C(C)C1=CC=CC=C1 COFMBBYARPOGBA-UHFFFAOYSA-N 0.000 description 1
ULIMZYAYESNNIP-UHFFFAOYSA-N 2-(methylamino)-2-phenylethanol Chemical compound CNC(CO)C1=CC=CC=C1 ULIMZYAYESNNIP-UHFFFAOYSA-N 0.000 description 1
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 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
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000012267 brine Substances 0.000 description 1
238000005515 capillary zone electrophoresis Methods 0.000 description 1
150000001728 carbonyl compounds Chemical class 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
230000009918 complex formation Effects 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
238000004821 distillation Methods 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000000605 extraction Methods 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
125000002541 furyl group Chemical group 0.000 description 1
125000005842 heteroatom Chemical group 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
125000002632 imidazolidinyl group Chemical group 0.000 description 1
125000002636 imidazolinyl group Chemical group 0.000 description 1
125000002883 imidazolyl group Chemical group 0.000 description 1
229910021432 inorganic complex Inorganic materials 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
125000001786 isothiazolyl group Chemical group 0.000 description 1
125000000842 isoxazolyl group Chemical group 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
229920005610 lignin Polymers 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
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
150000002902 organometallic compounds Chemical class 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
UCUUFSAXZMGPGH-UHFFFAOYSA-N penta-1,4-dien-3-one Chemical class C=CC(=O)C=C UCUUFSAXZMGPGH-UHFFFAOYSA-N 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
150000003003 phosphines Chemical class 0.000 description 1
125000004193 piperazinyl group Chemical group 0.000 description 1
125000005936 piperidyl group Chemical group 0.000 description 1
DJEHXEMURTVAOE-UHFFFAOYSA-M potassium bisulfite Chemical compound [K+].OS([O-])=O DJEHXEMURTVAOE-UHFFFAOYSA-M 0.000 description 1
229940099427 potassium bisulfite Drugs 0.000 description 1
235000010259 potassium hydrogen sulphite Nutrition 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
125000003373 pyrazinyl group Chemical group 0.000 description 1
125000003072 pyrazolidinyl group Chemical group 0.000 description 1
125000002755 pyrazolinyl group Chemical group 0.000 description 1
125000003226 pyrazolyl group Chemical group 0.000 description 1
125000002098 pyridazinyl group Chemical group 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
125000000719 pyrrolidinyl group Chemical group 0.000 description 1
125000001422 pyrrolinyl group Chemical group 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000002002 slurry Substances 0.000 description 1
229940079827 sodium hydrogen sulfite Drugs 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
125000000547 substituted alkyl group Chemical group 0.000 description 1
125000003107 substituted aryl group Chemical group 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 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
125000001544 thienyl group Chemical group 0.000 description 1
239000002023 wood Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
- C07C309/24—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of a carbon skeleton containing six-membered aromatic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B57/00—Separation of optically-active compounds
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

NL1012865A 1999-08-19 1999-08-19 1-Fenyl-3-oxopropaan-1-sulfonzuren en -sulfonaten en zuivere enantiomeren daarvan. NL1012865C2 (nl)

Priority Applications (8)

Application Number	Priority Date	Filing Date	Title
NL1012865A NL1012865C2 (nl)	1999-08-19	1999-08-19	1-Fenyl-3-oxopropaan-1-sulfonzuren en -sulfonaten en zuivere enantiomeren daarvan.
AU66010/00A AU6601000A (en)	1999-08-19	2000-08-18	3-oxopropane-1-sulphonic acids and sulphonates
DE60015353T DE60015353D1 (de)	1999-08-19	2000-08-18	3-oxo-1-propansulfonsäure und -sulfonate
JP2001518417A JP2003507452A (ja)	1999-08-19	2000-08-18	３−オキソプロパン−１−スルホン酸およびスルホネート
AT00953585T ATE280755T1 (de)	1999-08-19	2000-08-18	3-oxo-1-propansulfonsäure und -sulfonate
PCT/NL2000/000577 WO2001014327A1 (en)	1999-08-19	2000-08-18	3-oxopropane-1-sulphonic acids and sulphonates
EP20000953585 EP1204636B1 (de)	1999-08-19	2000-08-18	3-oxo-1-propansulfonsäure und -sulfonate
US10/069,167 US6639103B1 (en)	1999-08-19	2000-08-18	3-oxopropane-1-sulphonic acids and sulphonates

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
NL1012865		1999-08-19
NL1012865A NL1012865C2 (nl)	1999-08-19	1999-08-19	1-Fenyl-3-oxopropaan-1-sulfonzuren en -sulfonaten en zuivere enantiomeren daarvan.

Publications (1)

Publication Number	Publication Date
NL1012865C2 true NL1012865C2 (nl)	2001-02-20

Family

ID=19769757

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL1012865A NL1012865C2 (nl)	1999-08-19	1999-08-19	1-Fenyl-3-oxopropaan-1-sulfonzuren en -sulfonaten en zuivere enantiomeren daarvan.

Country Status (8)

Country	Link
US (1)	US6639103B1 (de)
EP (1)	EP1204636B1 (de)
JP (1)	JP2003507452A (de)
AT (1)	ATE280755T1 (de)
AU (1)	AU6601000A (de)
DE (1)	DE60015353D1 (de)
NL (1)	NL1012865C2 (de)
WO (1)	WO2001014327A1 (de)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NL1021844C2 (nl)	2002-11-05	2004-05-07	Alcoa Nederland Bv	Dek voor een kas of warenhuis.
NL1023098C2 (nl)	2002-11-05	2004-05-07	Alcoa Nederland Bv	Dek voor een kas of warenhuis.

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP2196456A1 (de) *	2008-12-11	2010-06-16	Royal College of Surgeons in Ireland	Verfahren zur Herstellung von schwefelhaltigen Verbindungen
CN102241555B (zh) *	2010-05-13	2013-06-05	山东谛爱生物技术股份有限公司	一种拆分制备光活氨基酸的方法

Citations (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH0812645A (ja) *	1994-06-23	1996-01-16	Tanabe Seiyaku Co Ltd	光学活性スルホン酸誘導体およびその製法

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2455282A (en) *	1945-09-15	1948-11-30	American Cyanamid Co	Processes of preparing insolubilized sulfonates and products thereof
NL1004346C2 (nl) *	1996-10-23	1998-04-24	Dsm Nv	Werkwijze voor het scheiden van een mengsel van enantiomeren in een geschikt oplosmiddel.

1999
- 1999-08-19 NL NL1012865A patent/NL1012865C2/nl not_active IP Right Cessation
2000
- 2000-08-18 AU AU66010/00A patent/AU6601000A/en not_active Abandoned
- 2000-08-18 WO PCT/NL2000/000577 patent/WO2001014327A1/en not_active Ceased
- 2000-08-18 DE DE60015353T patent/DE60015353D1/de not_active Expired - Lifetime
- 2000-08-18 US US10/069,167 patent/US6639103B1/en not_active Expired - Fee Related
- 2000-08-18 AT AT00953585T patent/ATE280755T1/de not_active IP Right Cessation
- 2000-08-18 EP EP20000953585 patent/EP1204636B1/de not_active Expired - Lifetime
- 2000-08-18 JP JP2001518417A patent/JP2003507452A/ja active Pending

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH0812645A (ja) *	1994-06-23	1996-01-16	Tanabe Seiyaku Co Ltd	光学活性スルホン酸誘導体およびその製法

Non-Patent Citations (12)

* Cited by examiner, † Cited by third party
Title
D.W. GLENNIE: "Chemical structure of Lignin sulphonates", TAPPI, vol. 46, no. 6, June 1966 (1966-06-01), Technical Assosiation of the Pulp and Paper Industry, Atlanta, US, pages 237 - 243, XP002137069 *
G. MESHITSUKA, ET AL.: "Studies on double bonds in lignosulphonate: existence of chalcone structure in lignosulphonate", PULP AND PAPER MAGAZINE CANADA, vol. 73, no. 6, June 1972 (1972-06-01), Westmount, CA, pages 61 - 64, XP000905231, ISSN: 0033-4103 *
H. RICHTZENHAIN, ET AL.: "Über Ligninmodellsubstanzen", CHEMISCHE BERICHTE, vol. 89, no. 2, 1956, Verlag Chemie, Weinheim, DE, pages 378 - 385, XP002137072, ISSN: 0009-2940 *
H. RICHTZENHAIN: "Die spaltung von Ätherbindungen mit Bisufit und Thioglykolsäure. Modelle zur Chimie des Lignins. XXVII. Mitteil. über Lignin", BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, vol. 72, no. 12, 6 December 1939 (1939-12-06), Verlag Chemie, Weinheim, DE, pages 2152 - 2160, XP002137073 *
H.A. SCHROEDER: "Paper chromatography of monomeric and dimeric lignin-type sulphonates", JOURNAL OF CHROMATOGRAPHY, vol. 63, no. 2, 23 December 1971 (1971-12-23), Elsevier Science Publishers, Amsterdam, NL, pages 470 - 474, XP002137070, ISSN: 0021-9673 *
K. KRATZL, ET AL.: "Über das Bauprinzip der Seitenketten der Ligninsulfonäuren. I", MONATSHEFTE FÜR CHEMIE, vol. 78, 1948, Springer Verlag, Wenen, AT, pages 376 - 391, XP000865948, ISSN: 0026-9247 *
K. KRATZL, ET AL.: "Über die Sulfitkochung von Phenylpropanderivaten und Chalkonen", BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, vol. 77, no. 6-7, 1944, Verlag Chemie, Weinheim, DE, pages 519 - 527, XP000905546 *
K.-H. PFOERTNER: "Substituierte Alkylsulfonate durch Addition von Natriumhydrogensulfit an Chalkone", HELVETICA CHIMICA ACTA, vol. 63, no. 3, 23 April 1980 (1980-04-23), Verlag Helvetica Chimica Acta, Basel, CH, pages 664 - 667, XP002137071, ISSN: 0018-019X *
M.F. BROWNE, ET AL.: "Model compounds for comparison with lignin. I. Preparation and properties of 8-methoxy-6-methylflavanone and 2'-hydroxy-3'-methoxy-5'-methylchalcone", JOURNAL OF ORGANIC CHEMISTRY, vol. 22, no. 11, 12 November 1957 (1957-11-12), American Chemical Society, Washington, DC, US, pages 1320 - 1322, XP002137074, ISSN: 0022-3263 *
O. DAHLMAN, ET AL.: "Analysis of low molecular weight lignin-derived sulphonates by capillary zone electrophoresis", JOURNAL OF WOOD CHEMISTRY AND TECHNOLOGY, vol. 16, no. 1, 1996, Marcel Dekker, New York, NY, US, pages 47 - 60, XP000865513, ISSN: 0277-3813 *
PATENT ABSTRACTS OF JAPAN vol. 1996, no. 05 31 May 1996 (1996-05-31) *
S. RACHWAL: "Addition of amine hydrosulphites to vinyl ketones. Conformation of the gamma-oxoalkanesulphonate anions", ZESZYTY NAUKOWE UNIWERSYTET JAGIELLONSKIEGO, PRACE CHEMICZNE, vol. 32, 1989, Uniwersytet Jagielonski, Krakow, PL, pages 93 - 104, XP000865511, ISSN: 0083-4319 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NL1021844C2 (nl)	2002-11-05	2004-05-07	Alcoa Nederland Bv	Dek voor een kas of warenhuis.
NL1023098C2 (nl)	2002-11-05	2004-05-07	Alcoa Nederland Bv	Dek voor een kas of warenhuis.

Also Published As

Publication number	Publication date
DE60015353D1 (de)	2004-12-02
US6639103B1 (en)	2003-10-28
ATE280755T1 (de)	2004-11-15
EP1204636B1 (de)	2004-10-27
WO2001014327A1 (en)	2001-03-01
JP2003507452A (ja)	2003-02-25
AU6601000A (en)	2001-03-19
EP1204636A1 (de)	2002-05-15

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Date	Code	Title	Description
2001-04-02	PD2B	A search report has been drawn up
2004-05-03	VD1	Lapsed due to non-payment of the annual fee	Effective date: 20040301

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NL1012865C2 - 1-Fenyl-3-oxopropaan-1-sulfonzuren en -sulfonaten en zuivere enantiomeren daarvan. - Google Patents

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Priority Applications (8)

Applications Claiming Priority (2)

Publications (1)

Family

ID=19769757

Family Applications (1)

Country Status (8)

Cited By (2)

Families Citing this family (2)

Citations (1)

Family Cites Families (2)

Patent Citations (1)

Non-Patent Citations (12)

Cited By (2)

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