AU2001277231A1 - Kinetic resolutions of chiral 2- and 3-substituted carboxylic acids - Google Patents
Kinetic resolutions of chiral 2- and 3-substituted carboxylic acidsInfo
- Publication number
- AU2001277231A1 AU2001277231A1 AU2001277231A AU7723101A AU2001277231A1 AU 2001277231 A1 AU2001277231 A1 AU 2001277231A1 AU 2001277231 A AU2001277231 A AU 2001277231A AU 7723101 A AU7723101 A AU 7723101A AU 2001277231 A1 AU2001277231 A1 AU 2001277231A1
- Authority
- AU
- Australia
- Prior art keywords
- racemic
- chiral
- present
- kinetic resolution
- carboxylic acids
- 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.)
- Abandoned
Links
- 150000001735 carboxylic acids Chemical class 0.000 title 1
- 239000000203 mixture Substances 0.000 abstract 5
- 238000000034 method Methods 0.000 abstract 4
- 239000000758 substrate Substances 0.000 abstract 2
- 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 abstract 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 150000001576 beta-amino acids Chemical group 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 150000005676 cyclic carbonates Chemical class 0.000 abstract 1
- 125000004122 cyclic group Chemical group 0.000 abstract 1
- 238000011067 equilibration Methods 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 238000011065 in-situ storage Methods 0.000 abstract 1
- 239000012038 nucleophile Substances 0.000 abstract 1
- 150000003512 tertiary amines Chemical class 0.000 abstract 1
- 150000003566 thiocarboxylic acids Chemical class 0.000 abstract 1
- 150000003573 thiols Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D263/18—Oxygen atoms
- C07D263/20—Oxygen atoms attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B53/00—Asymmetric syntheses
-
- 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
- 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
- C07C227/34—Preparation of optical isomers by separation of optical isomers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C269/00—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C269/06—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups by reactions not involving the formation of carbamate groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/487—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to chemical modification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/12—Preparation of carboxylic acid esters from asymmetrical anhydrides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/32—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D317/34—Oxygen atoms
- C07D317/36—Alkylene carbonates; Substituted alkylene carbonates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Analytical Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
- Fertilizers (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Epoxy Compounds (AREA)
Abstract
One aspect of the present invention relates to a method for the kinetic resolution of racemic and diastereomeric mixtures of chiral compounds. The critical elements of the method are: a non-racemic chiral tertiary-amine-containing catalyst; a racemic or diastereomeric mixture of a chiral substrate, e.g., a cyclic carbonate or cyclic carbamate; and a nucleophile, e.g., an alcohol, amine or thiol. A preferred embodiment of the present invention relates to a method for achieving the kinetic resolution of racemic and diastereomeric mixtures of derivatives of α- and β-amino, hydroxy, and thio carboxylic acids. In certain embodiments, the methods of the present invention achieve dynamic kinetic resolution of a racemic or diastereomeric mixture of a substrate, i.e., a kinetic resolution wherein the yield of the resolved enantiomer or diastereomer, respectively, exceeds the amount present in the original mixture due to the in situ equilibration of the enantiomers or diastereomers under the reaction conditions prior to the resolution step.
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US22214500P | 2000-07-31 | 2000-07-31 | |
US60222145 | 2000-07-31 | ||
US25317200P | 2000-11-27 | 2000-11-27 | |
US60253172 | 2000-11-27 | ||
PCT/US2001/023953 WO2002010096A1 (en) | 2000-07-31 | 2001-07-31 | Kinetic resolutions of chiral 2- and 3-substituted carboxylic acids |
Publications (1)
Publication Number | Publication Date |
---|---|
AU2001277231A1 true AU2001277231A1 (en) | 2002-02-13 |
Family
ID=26916484
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
AU2001277231A Abandoned AU2001277231A1 (en) | 2000-07-31 | 2001-07-31 | Kinetic resolutions of chiral 2- and 3-substituted carboxylic acids |
Country Status (9)
Country | Link |
---|---|
US (4) | US6562966B2 (en) |
EP (1) | EP1305270B1 (en) |
JP (1) | JP2004505098A (en) |
KR (1) | KR100799789B1 (en) |
AT (1) | ATE264282T1 (en) |
AU (1) | AU2001277231A1 (en) |
CA (1) | CA2416303A1 (en) |
DE (1) | DE60102825T2 (en) |
WO (1) | WO2002010096A1 (en) |
Families Citing this family (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2002002538A1 (en) * | 2000-07-04 | 2002-01-10 | Mitsui Chemicals, Inc. | Amino acid-n-carboxy anhydrides hvaing substituent at nitrogen |
EP1305270B1 (en) * | 2000-07-31 | 2004-04-14 | Brandeis University | Kinetic resolutions of chiral 2- and 3-substituted carboxylic acids |
KR20040030905A (en) * | 2001-07-31 | 2004-04-09 | 브랜데이스 유니버시티 | Kinetic resolutions of chirat 3- and 3-substituted carboxylic acids |
TWI298067B (en) * | 2002-01-31 | 2008-06-21 | Daiso Co Ltd | New optically active compound, method for kinetic resolution of carbonic acid derivatives and catalyst thereof |
US7531662B2 (en) | 2003-06-11 | 2009-05-12 | Brandeis University | Cinchona-alkaloid-based catalysts, and asymmetric alcoholysis of cyclic anhydrides using them |
US8540755B2 (en) | 2003-07-21 | 2013-09-24 | Robin C. Whitmore | Self-drilling self-tapping bone screw |
JP4591998B2 (en) * | 2004-07-30 | 2010-12-01 | 日本曹達株式会社 | Method for producing optically active alcohol derivative |
US7675628B2 (en) * | 2006-09-07 | 2010-03-09 | 4D Technology Corporation | Synchronous frequency-shift mechanism in Fizeau interferometer |
US8345258B2 (en) * | 2006-09-07 | 2013-01-01 | 4 D Technology Corporation | Synchronous frequency-shift mechanism in fizeau interferometer |
CA2853024C (en) | 2011-11-11 | 2017-08-22 | Pfizer Inc. | 2-thiopyrimidinones |
KR20170129769A (en) | 2015-03-17 | 2017-11-27 | 리제너론 파아마슈티컬스, 인크. | Amino acid acylation reagents and methods for their use |
JP2018515480A (en) | 2015-05-05 | 2018-06-14 | ファイザー・インク | 2-thiopyrimidinone |
KR20170037240A (en) * | 2015-09-25 | 2017-04-04 | 주식회사 아미노로직스 | Method for the Preparation of the Optically Active Thienylalanine |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
IT1240651B (en) * | 1990-05-17 | 1993-12-17 | Zambon Spa | PROCESS FOR THE RESOLUTION OF GLYCIDIC DERIVATIVES |
US6262278B1 (en) * | 1995-03-14 | 2001-07-17 | President And Fellows Of Harvard College | Stereoselective ring opening reactions |
US5665890A (en) | 1995-03-14 | 1997-09-09 | President And Fellows Of Harvard College | Stereoselective ring opening reactions |
DE19617772A1 (en) * | 1996-05-03 | 1997-11-13 | Bayer Ag | New efficient and highly enantioselective process for the production of enantiomerically pure cyclopentane-beta-amino acids |
US6521561B1 (en) * | 1998-05-01 | 2003-02-18 | President And Fellows Of Harvard College | Main-group metal based asymmetric catalysts and applications thereof |
US6562967B2 (en) * | 2000-07-31 | 2003-05-13 | Brandeis University | Kinetic resolutions of chiral 2-and-3-substituted carboxylic acids |
EP1305270B1 (en) * | 2000-07-31 | 2004-04-14 | Brandeis University | Kinetic resolutions of chiral 2- and 3-substituted carboxylic acids |
-
2001
- 2001-07-31 EP EP01955023A patent/EP1305270B1/en not_active Expired - Lifetime
- 2001-07-31 DE DE60102825T patent/DE60102825T2/en not_active Expired - Fee Related
- 2001-07-31 AU AU2001277231A patent/AU2001277231A1/en not_active Abandoned
- 2001-07-31 CA CA002416303A patent/CA2416303A1/en not_active Abandoned
- 2001-07-31 WO PCT/US2001/023953 patent/WO2002010096A1/en active IP Right Grant
- 2001-07-31 US US09/919,371 patent/US6562966B2/en not_active Expired - Lifetime
- 2001-07-31 KR KR1020037001408A patent/KR100799789B1/en not_active IP Right Cessation
- 2001-07-31 AT AT01955023T patent/ATE264282T1/en not_active IP Right Cessation
- 2001-07-31 JP JP2002516229A patent/JP2004505098A/en not_active Abandoned
-
2002
- 2002-11-20 US US10/300,704 patent/US6743914B2/en not_active Expired - Lifetime
-
2004
- 2004-05-26 US US10/854,737 patent/US7057038B2/en not_active Expired - Fee Related
-
2006
- 2006-06-05 US US11/447,237 patent/US7767811B2/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
US20060293536A1 (en) | 2006-12-28 |
CA2416303A1 (en) | 2002-02-07 |
US7057038B2 (en) | 2006-06-06 |
KR100799789B1 (en) | 2008-01-31 |
US7767811B2 (en) | 2010-08-03 |
US6743914B2 (en) | 2004-06-01 |
JP2004505098A (en) | 2004-02-19 |
WO2002010096A1 (en) | 2002-02-07 |
US20020165393A1 (en) | 2002-11-07 |
US6562966B2 (en) | 2003-05-13 |
DE60102825D1 (en) | 2004-05-19 |
ATE264282T1 (en) | 2004-04-15 |
DE60102825T2 (en) | 2005-03-31 |
EP1305270B1 (en) | 2004-04-14 |
KR20030020430A (en) | 2003-03-08 |
US20050020849A1 (en) | 2005-01-27 |
US20030166963A1 (en) | 2003-09-04 |
EP1305270A1 (en) | 2003-05-02 |
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