JP2005520570A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2005520570A5 JP2005520570A5 JP2003580559A JP2003580559A JP2005520570A5 JP 2005520570 A5 JP2005520570 A5 JP 2005520570A5 JP 2003580559 A JP2003580559 A JP 2003580559A JP 2003580559 A JP2003580559 A JP 2003580559A JP 2005520570 A5 JP2005520570 A5 JP 2005520570A5
- Authority
- JP
- Japan
- Prior art keywords
- propylene glycol
- enantiomer
- substrate
- glycol ether
- reaction mixture
- Prior art date
- Legal status (The legal status 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 status listed.)
- Pending
Links
- 125000002252 acyl group Chemical group 0.000 claims description 19
- 238000006243 chemical reaction Methods 0.000 claims description 17
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 12
- 239000003054 catalyst Substances 0.000 claims description 7
- 238000000034 method Methods 0.000 claims 56
- 239000000758 substrate Substances 0.000 claims 21
- 239000011541 reaction mixture Substances 0.000 claims 17
- 108090001060 Lipase Proteins 0.000 claims 15
- 102000004882 Lipase Human genes 0.000 claims 15
- 239000004367 Lipase Substances 0.000 claims 15
- 235000019421 lipase Nutrition 0.000 claims 15
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims 14
- -1 enol ester Chemical class 0.000 claims 11
- JDSQBDGCMUXRBM-UHFFFAOYSA-N 2-[2-(2-butoxypropoxy)propoxy]propan-1-ol Chemical compound CCCCOC(C)COC(C)COC(C)CO JDSQBDGCMUXRBM-UHFFFAOYSA-N 0.000 claims 10
- 102000004157 Hydrolases Human genes 0.000 claims 9
- 108090000604 Hydrolases Proteins 0.000 claims 9
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 6
- 235000013772 propylene glycol Nutrition 0.000 claims 6
- 241001661345 Moesziomyces antarcticus Species 0.000 claims 5
- 125000000217 alkyl group Chemical group 0.000 claims 5
- 210000002196 fr. b Anatomy 0.000 claims 5
- 125000003118 aryl group Chemical group 0.000 claims 4
- 150000002148 esters Chemical class 0.000 claims 4
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 claims 3
- ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 claims 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims 3
- 102000004190 Enzymes Human genes 0.000 claims 3
- 108090000790 Enzymes Proteins 0.000 claims 3
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical group CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims 3
- 239000003377 acid catalyst Substances 0.000 claims 3
- 150000008064 anhydrides Chemical class 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- 238000004064 recycling Methods 0.000 claims 3
- 238000005809 transesterification reaction Methods 0.000 claims 3
- GQCZPFJGIXHZMB-LURJTMIESA-N (2s)-1-[(2-methylpropan-2-yl)oxy]propan-2-ol Chemical compound C[C@H](O)COC(C)(C)C GQCZPFJGIXHZMB-LURJTMIESA-N 0.000 claims 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 2
- 108090000371 Esterases Proteins 0.000 claims 2
- HETCEOQFVDFGSY-UHFFFAOYSA-N Isopropenyl acetate Chemical compound CC(=C)OC(C)=O HETCEOQFVDFGSY-UHFFFAOYSA-N 0.000 claims 2
- 241000589774 Pseudomonas sp. Species 0.000 claims 2
- 125000004036 acetal group Chemical group 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 claims 2
- 238000004821 distillation Methods 0.000 claims 2
- 239000000047 product Substances 0.000 claims 2
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims 1
- JLIDRDJNLAWIKT-UHFFFAOYSA-N 1,2-dimethyl-3h-benzo[e]indole Chemical compound C1=CC=CC2=C(C(=C(C)N3)C)C3=CC=C21 JLIDRDJNLAWIKT-UHFFFAOYSA-N 0.000 claims 1
- NPJNWZWXHBINFR-UHFFFAOYSA-N 1-ethoxyethenyl acetate Chemical compound CCOC(=C)OC(C)=O NPJNWZWXHBINFR-UHFFFAOYSA-N 0.000 claims 1
- LIPRQQHINVWJCH-UHFFFAOYSA-N 1-ethoxypropan-2-yl acetate Chemical compound CCOCC(C)OC(C)=O LIPRQQHINVWJCH-UHFFFAOYSA-N 0.000 claims 1
- DMFAHCVITRDZQB-UHFFFAOYSA-N 1-propoxypropan-2-yl acetate Chemical compound CCCOCC(C)OC(C)=O DMFAHCVITRDZQB-UHFFFAOYSA-N 0.000 claims 1
- GQCZPFJGIXHZMB-UHFFFAOYSA-N 1-tert-Butoxy-2-propanol Chemical compound CC(O)COC(C)(C)C GQCZPFJGIXHZMB-UHFFFAOYSA-N 0.000 claims 1
- XHAXVDWUMCHTCY-UHFFFAOYSA-N 2,2,2-trichloroethyl acetate Chemical compound CC(=O)OCC(Cl)(Cl)Cl XHAXVDWUMCHTCY-UHFFFAOYSA-N 0.000 claims 1
- ZOWSJJBOQDKOHI-UHFFFAOYSA-N 2,2,2-trifluoroethyl acetate Chemical compound CC(=O)OCC(F)(F)F ZOWSJJBOQDKOHI-UHFFFAOYSA-N 0.000 claims 1
- DEXWRCYOMLUJRF-UHFFFAOYSA-N 2,2,2-trifluoroethyl butanoate Chemical compound CCCC(=O)OCC(F)(F)F DEXWRCYOMLUJRF-UHFFFAOYSA-N 0.000 claims 1
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- 108700023418 Amidases Proteins 0.000 claims 1
- 241000589513 Burkholderia cepacia Species 0.000 claims 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 108010013563 Lipoprotein Lipase Proteins 0.000 claims 1
- 102100022119 Lipoprotein lipase Human genes 0.000 claims 1
- 108091005804 Peptidases Proteins 0.000 claims 1
- 239000004365 Protease Substances 0.000 claims 1
- 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 claims 1
- 150000001242 acetic acid derivatives Chemical class 0.000 claims 1
- DULCUDSUACXJJC-UHFFFAOYSA-N benzeneacetic acid ethyl ester Natural products CCOC(=O)CC1=CC=CC=C1 DULCUDSUACXJJC-UHFFFAOYSA-N 0.000 claims 1
- 239000006227 byproduct Substances 0.000 claims 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims 1
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 claims 1
- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 claims 1
- JLEKJZUYWFJPMB-UHFFFAOYSA-N ethyl 2-methoxyacetate Chemical compound CCOC(=O)COC JLEKJZUYWFJPMB-UHFFFAOYSA-N 0.000 claims 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 239000003456 ion exchange resin Substances 0.000 claims 1
- 229920003303 ion-exchange polymer Polymers 0.000 claims 1
- JJTUDXZGHPGLLC-UHFFFAOYSA-N lactide Chemical compound CC1OC(=O)C(C)OC1=O JJTUDXZGHPGLLC-UHFFFAOYSA-N 0.000 claims 1
- 239000011159 matrix material Substances 0.000 claims 1
- 238000012544 monitoring process Methods 0.000 claims 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 claims 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 claims 1
- 229940014800 succinic anhydride Drugs 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 238000005356 chiral GC Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 229920002545 silicone oil Polymers 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- CICOZWHZVMOPJS-UHFFFAOYSA-N s-Phenylmercapturic acid Chemical class CC(=O)NC(C(O)=O)CSC1=CC=CC=C1 CICOZWHZVMOPJS-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US36676702P | 2002-03-22 | 2002-03-22 | |
| PCT/US2003/008941 WO2003083126A2 (en) | 2002-03-22 | 2003-03-21 | Enzymatic resolution of propylene glycol alkyl (or aryl) ethers and ether acetates |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2005520570A JP2005520570A (ja) | 2005-07-14 |
| JP2005520570A5 true JP2005520570A5 (enExample) | 2006-05-18 |
Family
ID=28675281
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003580559A Pending JP2005520570A (ja) | 2002-03-22 | 2003-03-21 | プロピレングリコールアルキル（又はアリール）エーテル及びエーテルアセテートの酵素分割 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US7264960B2 (enExample) |
| EP (1) | EP1490501B1 (enExample) |
| JP (1) | JP2005520570A (enExample) |
| KR (1) | KR20040099348A (enExample) |
| CN (1) | CN1656230B (enExample) |
| AT (1) | ATE469237T1 (enExample) |
| AU (1) | AU2003222053A1 (enExample) |
| DE (1) | DE60332714D1 (enExample) |
| WO (1) | WO2003083126A2 (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005095629A1 (en) * | 2004-03-29 | 2005-10-13 | Dsm Ip Assets B.V. | Process for the preparation of enantiomerically enriched esters and alcohols by means of azeotropically dried enzyme compositions |
| US7570651B2 (en) * | 2004-06-16 | 2009-08-04 | Siamack Haghighi | High-performance reconfigurable interconnect for concurrent operation of multiple systems |
| KR100650798B1 (ko) * | 2004-07-19 | 2006-11-27 | (주)제이코통상 | 광학활성 카복실산의 제조방법 |
| KR100650797B1 (ko) * | 2005-12-12 | 2006-11-27 | (주)케미코월드 | 광학활성 사이클로프로판 카복사미드의 제조방법 |
| CN100427608C (zh) * | 2006-11-08 | 2008-10-22 | 浙江大学 | 酶法拆分制备光学活性烯丙基呋喃甲醇的方法 |
| EP2655646A4 (en) * | 2010-12-20 | 2014-05-21 | Du Pont | TARGETED PERHYDROLASES |
| DE102011107959A1 (de) * | 2011-07-20 | 2013-01-24 | Thyssenkrupp Uhde Gmbh | Herstellung von optisch reinem Propan-1,2-diol |
| CN114058655B (zh) * | 2021-11-30 | 2023-08-29 | 青岛科技大学 | 一种酶-化学一锅法合成(r)-乙酰胺基苯丙醇的方法 |
| WO2024021261A1 (zh) * | 2022-07-29 | 2024-02-01 | 上海皓元医药股份有限公司 | 一种艾日布林中间体的制备方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5541080A (en) | 1991-11-01 | 1996-07-30 | Wisconsin Alumni Research Fdn. | Method for preparing L-alpha-amino acids |
| JP3874035B2 (ja) * | 1996-06-26 | 2007-01-31 | 三菱瓦斯化学株式会社 | 光学活性２級アルコールの製造法 |
| JP2000063312A (ja) * | 1998-08-17 | 2000-02-29 | Mitsubishi Gas Chem Co Inc | 光学活性２級アルコール及びその製造法 |
-
2003
- 2003-03-21 US US10/502,692 patent/US7264960B2/en not_active Expired - Fee Related
- 2003-03-21 WO PCT/US2003/008941 patent/WO2003083126A2/en not_active Ceased
- 2003-03-21 KR KR10-2004-7014868A patent/KR20040099348A/ko not_active Withdrawn
- 2003-03-21 DE DE60332714T patent/DE60332714D1/de not_active Expired - Lifetime
- 2003-03-21 AU AU2003222053A patent/AU2003222053A1/en not_active Abandoned
- 2003-03-21 EP EP03718037A patent/EP1490501B1/en not_active Expired - Lifetime
- 2003-03-21 AT AT03718037T patent/ATE469237T1/de not_active IP Right Cessation
- 2003-03-21 JP JP2003580559A patent/JP2005520570A/ja active Pending
- 2003-03-21 CN CN038067668A patent/CN1656230B/zh not_active Expired - Fee Related
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2005520570A5 (enExample) | ||
| JP3010497B2 (ja) | 光学活性α―ヒドロキシエステル類の製造方法 | |
| JP2014522652A5 (enExample) | ||
| JP2014522652A (ja) | 分離方法 | |
| Lin et al. | Dynamic kinetic resolution of suprofen thioester via coupled trioctylamine and lipase catalysis | |
| KR100657212B1 (ko) | 라세믹 에스테르로부터 광학활성 에스테르 유도체와 이의 산의 제조 방법 | |
| CA2322842A1 (en) | Process for the enzymatic separation of enantiomers of 3(r)- and 3(s)-hydroxy-1-methyl-4-(2,4,6-trimethoxyphenyl)-1,2,3,6-tetrahydropyridine or its carboxylic acid esters | |
| JP2005520570A (ja) | プロピレングリコールアルキル（又はアリール）エーテル及びエーテルアセテートの酵素分割 | |
| JP2726114B2 (ja) | 光学活性３―クロロ―１，２―プロパンジオールおよびそのエステルの製造法 | |
| JP2690953B2 (ja) | 光学活性１，３−ブタンジオールおよびその誘導体の製造法 | |
| CA2145230A1 (en) | Enzymatic resolution of asymmetric alcohols by means of vinyl esters of polybasic carboxylic acids | |
| JP6287528B2 (ja) | 光学活性３，３−ジフルオロ乳酸誘導体の製造方法 | |
| JP3803587B2 (ja) | 鏡像異性的に純粋な１，３−ジオキソラン−４−オン誘導体若しくは１，３−オキサチオラン−５−オン−誘導体の酵素的製造方法 | |
| KR100650797B1 (ko) | 광학활성 사이클로프로판 카복사미드의 제조방법 | |
| KR100748897B1 (ko) | 효소적 방법에 의한 광학활성 3-히드록시 부틸산 및 이의 에스테르 제조방법 | |
| JPH1014590A (ja) | 光学活性２−置換−３−フェニルプロピオン酸及びそのエステルの製造方法 | |
| JP3095539B2 (ja) | 光学活性α，β−エポキシカルボン酸およびそのエステルの製造法 | |
| EP1349950B1 (en) | A process for the preparation of 1-(3-trifluoromethylphenyl)-propan-2-ol enantiomers | |
| JP2816744B2 (ja) | 光学活性３―アリール―３―ヒドロキシプロピオン酸アルキルの製造法 | |
| JP3115911B2 (ja) | 光学活性２−スルホニルオキシ−シクロアルカノール類の製造方法 | |
| KR100453996B1 (ko) | 효소적 방법에 의한 광학활성 에틸 3-히드록시-3-페닐프로피오네이트 및 이의 에스테르 제조 방법 | |
| JP3122767B2 (ja) | 光学活性ハロヒドリン誘導体の製造方法 | |
| JP4461642B2 (ja) | 光学活性トランス−２−オキソ−４−オキサゾリジンカルボン酸及びエステル類の製造方法 | |
| Poppe et al. | Stereoselective and Stereospecific Reactions | |
| JPH10248593A (ja) | ω−アルコキシ−１，１，１−トリフルオロ−２−アルカノールの光学分割方法 |