SK55497A3 - Effective and enantiomerically high-selective method for producing enantiomerically pure cyclopentane-beta-amino acids - Google Patents
Effective and enantiomerically high-selective method for producing enantiomerically pure cyclopentane-beta-amino acids Download PDFInfo
- Publication number
- SK55497A3 SK55497A3 SK554-97A SK55497A SK55497A3 SK 55497 A3 SK55497 A3 SK 55497A3 SK 55497 A SK55497 A SK 55497A SK 55497 A3 SK55497 A3 SK 55497A3
- Authority
- SK
- Slovakia
- Prior art keywords
- formula
- group
- enantiomerically pure
- iva
- carbon atoms
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- 238000004519 manufacturing process Methods 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 41
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 23
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 23
- -1 beta -amino acid compounds Chemical class 0.000 claims abstract description 17
- 238000006243 chemical reaction Methods 0.000 claims abstract description 16
- 150000002148 esters Chemical class 0.000 claims abstract description 16
- 239000002585 base Substances 0.000 claims abstract description 15
- 150000001412 amines Chemical class 0.000 claims abstract description 13
- 239000012442 inert solvent Substances 0.000 claims abstract description 12
- 238000006969 Curtius rearrangement reaction Methods 0.000 claims abstract description 10
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 9
- 238000003776 cleavage reaction Methods 0.000 claims abstract description 9
- 238000002360 preparation method Methods 0.000 claims abstract description 9
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- 125000005843 halogen group Chemical group 0.000 claims abstract description 8
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 5
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- 230000004913 activation Effects 0.000 claims abstract description 4
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 4
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 4
- 125000002252 acyl group Chemical group 0.000 claims abstract description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 3
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims abstract description 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims abstract description 3
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- 238000000034 method Methods 0.000 claims description 25
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- 230000008569 process Effects 0.000 claims description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
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- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims 2
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- 150000008065 acid anhydrides Chemical class 0.000 claims 1
- 239000002253 acid Substances 0.000 abstract description 5
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 abstract 2
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- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- KMPWYEUPVWOPIM-KODHJQJWSA-N cinchonidine Chemical compound C1=CC=C2C([C@H]([C@H]3[N@]4CC[C@H]([C@H](C4)C=C)C3)O)=CC=NC2=C1 KMPWYEUPVWOPIM-KODHJQJWSA-N 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- UCQFCFPECQILOL-UHFFFAOYSA-N diethyl hydrogen phosphate Chemical group CCOP(O)(=O)OCC UCQFCFPECQILOL-UHFFFAOYSA-N 0.000 description 1
- BADXJIPKFRBFOT-UHFFFAOYSA-N dimedone Chemical compound CC1(C)CC(=O)CC(=O)C1 BADXJIPKFRBFOT-UHFFFAOYSA-N 0.000 description 1
- LXQXGFPPYLKKSD-UHFFFAOYSA-L disodium;2,2-diethylpropanedioate Chemical compound [Na+].[Na+].CCC(CC)(C([O-])=O)C([O-])=O LXQXGFPPYLKKSD-UHFFFAOYSA-L 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 229960000811 hydroquinidine Drugs 0.000 description 1
- LJOQGZACKSYWCH-WZBLMQSHSA-N hydroquinine Chemical compound C1=C(OC)C=C2C([C@@H](O)[C@@H]3C[C@@H]4CCN3C[C@@H]4CC)=CC=NC2=C1 LJOQGZACKSYWCH-WZBLMQSHSA-N 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- WDWDWGRYHDPSDS-UHFFFAOYSA-N methanimine Chemical class N=C WDWDWGRYHDPSDS-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000010413 mother solution Substances 0.000 description 1
- KAHVZNKZQFSBFW-UHFFFAOYSA-N n-methyl-n-trimethylsilylmethanamine Chemical compound CN(C)[Si](C)(C)C KAHVZNKZQFSBFW-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- RKOUGZGFAYMUIO-RITPCOANSA-N pdl 118 Chemical compound N[C@H]1CC(=C)C[C@H]1C(O)=O RKOUGZGFAYMUIO-RITPCOANSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- WSDQIHATCCOMLH-UHFFFAOYSA-N phenyl n-(3,5-dichlorophenyl)carbamate Chemical compound ClC1=CC(Cl)=CC(NC(=O)OC=2C=CC=CC=2)=C1 WSDQIHATCCOMLH-UHFFFAOYSA-N 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- VYPDUQYOLCLEGS-UHFFFAOYSA-M sodium;2-ethylhexanoate Chemical compound [Na+].CCCCC(CC)C([O-])=O VYPDUQYOLCLEGS-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 1
- IGNTWNVBGLNYDV-UHFFFAOYSA-N triisopropylphosphine Chemical compound CC(C)P(C(C)C)C(C)C IGNTWNVBGLNYDV-UHFFFAOYSA-N 0.000 description 1
- SEDZOYHHAIAQIW-UHFFFAOYSA-N trimethylsilyl azide Chemical compound C[Si](C)(C)N=[N+]=[N-] SEDZOYHHAIAQIW-UHFFFAOYSA-N 0.000 description 1
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/30—Preparation of optical isomers
- C07C227/32—Preparation of optical isomers by stereospecific synthesis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/24—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a ring other than a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/74—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19617772A DE19617772A1 (de) | 1996-05-03 | 1996-05-03 | Neues effizientes und hochenantioselektives Verfahren zur Herstellung von enantiomerenreinen Cyclopentan-beta-aminosäuren |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK55497A3 true SK55497A3 (en) | 1997-11-05 |
Family
ID=7793231
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK554-97A SK55497A3 (en) | 1996-05-03 | 1997-05-02 | Effective and enantiomerically high-selective method for producing enantiomerically pure cyclopentane-beta-amino acids |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US5877343A (cs) |
| EP (1) | EP0805145B1 (cs) |
| JP (1) | JPH1087586A (cs) |
| KR (1) | KR970074749A (cs) |
| CN (1) | CN1168883A (cs) |
| AR (2) | AR006944A1 (cs) |
| AT (1) | ATE207876T1 (cs) |
| AU (1) | AU1915697A (cs) |
| BR (1) | BR9701983A (cs) |
| CA (1) | CA2204055A1 (cs) |
| CZ (1) | CZ135397A3 (cs) |
| DE (2) | DE19617772A1 (cs) |
| DK (1) | DK0805145T3 (cs) |
| ES (1) | ES2166930T3 (cs) |
| HR (1) | HRP970214A2 (cs) |
| HU (1) | HU9700831D0 (cs) |
| ID (1) | ID16859A (cs) |
| IL (1) | IL120747A0 (cs) |
| NO (1) | NO971983L (cs) |
| PL (1) | PL319775A1 (cs) |
| PT (1) | PT805145E (cs) |
| SI (1) | SI0805145T1 (cs) |
| SK (1) | SK55497A3 (cs) |
| SV (1) | SV1997000031A (cs) |
| ZA (1) | ZA973796B (cs) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6562966B2 (en) * | 2000-07-31 | 2003-05-13 | Brandeis University | Kinetic resolutions of chiral 2- and 3-substituted carboxylic acids |
| CA2456166A1 (en) * | 2001-07-31 | 2003-02-13 | Brandeis University | Kinetic resolutions of chiral 2- and 3-substituted carboxylic acids |
| US7531662B2 (en) * | 2003-06-11 | 2009-05-12 | Brandeis University | Cinchona-alkaloid-based catalysts, and asymmetric alcoholysis of cyclic anhydrides using them |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3560565A (en) * | 1969-06-03 | 1971-02-02 | American Home Prod | 1-amino-n-sulfonylcyclopentane-carboxamides |
| GB8716278D0 (en) * | 1987-07-10 | 1987-08-19 | Fujisawa Pharmaceutical Co | Antimicrobial agent |
| AU673824B2 (en) * | 1992-05-29 | 1996-11-28 | Bayer Aktiengesellschaft | Cyclopentane- and -pentene-beta-amino acids |
| DE4400749A1 (de) * | 1994-01-13 | 1995-07-20 | Bayer Ag | Neues hochenantioselektives Verfahren zur Herstellung von enantiomerenreinen Cyclopentan- und -penten-beta-Aminosäuren |
-
1996
- 1996-05-03 DE DE19617772A patent/DE19617772A1/de not_active Withdrawn
-
1997
- 1997-04-21 AT AT97106550T patent/ATE207876T1/de not_active IP Right Cessation
- 1997-04-21 SI SI9730164T patent/SI0805145T1/xx unknown
- 1997-04-21 PT PT97106550T patent/PT805145E/pt unknown
- 1997-04-21 EP EP97106550A patent/EP0805145B1/de not_active Expired - Lifetime
- 1997-04-21 DE DE59705135T patent/DE59705135D1/de not_active Expired - Fee Related
- 1997-04-21 ES ES97106550T patent/ES2166930T3/es not_active Expired - Lifetime
- 1997-04-21 DK DK97106550T patent/DK0805145T3/da active
- 1997-04-22 HR HR19617772.3A patent/HRP970214A2/xx not_active Application Discontinuation
- 1997-04-25 US US08/843,102 patent/US5877343A/en not_active Expired - Fee Related
- 1997-04-28 JP JP9122796A patent/JPH1087586A/ja active Pending
- 1997-04-29 NO NO971983A patent/NO971983L/no unknown
- 1997-04-29 AU AU19156/97A patent/AU1915697A/en not_active Abandoned
- 1997-04-30 PL PL97319775A patent/PL319775A1/xx unknown
- 1997-04-30 HU HU9700831A patent/HU9700831D0/hu unknown
- 1997-04-30 CN CN97109766A patent/CN1168883A/zh active Pending
- 1997-04-30 CA CA002204055A patent/CA2204055A1/en not_active Abandoned
- 1997-05-01 IL IL12074797A patent/IL120747A0/xx unknown
- 1997-05-02 KR KR1019970017032A patent/KR970074749A/ko not_active Withdrawn
- 1997-05-02 ZA ZA9703796A patent/ZA973796B/xx unknown
- 1997-05-02 SK SK554-97A patent/SK55497A3/sk unknown
- 1997-05-02 AR ARP970101819A patent/AR006944A1/es unknown
- 1997-05-02 ID IDP971474A patent/ID16859A/id unknown
- 1997-05-02 SV SV1997000031A patent/SV1997000031A/es unknown
- 1997-05-02 BR BR9701983A patent/BR9701983A/pt not_active Application Discontinuation
- 1997-05-02 CZ CZ971353A patent/CZ135397A3/cs unknown
-
1998
- 1998-03-20 AR ARP980101294A patent/AR013071A2/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NO971983L (no) | 1997-11-04 |
| SI0805145T1 (en) | 2002-02-28 |
| BR9701983A (pt) | 1998-09-15 |
| SV1997000031A (es) | 1997-10-23 |
| HU9700831D0 (en) | 1997-06-30 |
| JPH1087586A (ja) | 1998-04-07 |
| PL319775A1 (en) | 1997-11-10 |
| CN1168883A (zh) | 1997-12-31 |
| US5877343A (en) | 1999-03-02 |
| EP0805145A1 (de) | 1997-11-05 |
| NO971983D0 (no) | 1997-04-29 |
| DK0805145T3 (da) | 2002-03-04 |
| EP0805145B1 (de) | 2001-10-31 |
| MX9702768A (es) | 1997-11-29 |
| ATE207876T1 (de) | 2001-11-15 |
| CA2204055A1 (en) | 1997-11-03 |
| AU1915697A (en) | 1997-11-06 |
| AR006944A1 (es) | 1999-09-29 |
| KR970074749A (ko) | 1997-12-10 |
| HRP970214A2 (en) | 1998-04-30 |
| PT805145E (pt) | 2002-03-28 |
| ES2166930T3 (es) | 2002-05-01 |
| DE19617772A1 (de) | 1997-11-13 |
| AR013071A2 (es) | 2000-12-13 |
| ZA973796B (en) | 1997-12-01 |
| CZ135397A3 (cs) | 1998-05-13 |
| ID16859A (id) | 1997-11-20 |
| IL120747A0 (en) | 1997-09-30 |
| DE59705135D1 (de) | 2001-12-06 |
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