WO2003042132A1 - Recovery and recycling of chiral tartaric acid resolving agents - Google Patents

Recovery and recycling of chiral tartaric acid resolving agents Download PDF

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Publication number
WO2003042132A1
WO2003042132A1 PCT/EP2002/012494 EP0212494W WO03042132A1 WO 2003042132 A1 WO2003042132 A1 WO 2003042132A1 EP 0212494 W EP0212494 W EP 0212494W WO 03042132 A1 WO03042132 A1 WO 03042132A1
Authority
WO
WIPO (PCT)
Prior art keywords
tartaric acid
process according
acid
substituted
recovery
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.)
Ceased
Application number
PCT/EP2002/012494
Other languages
English (en)
French (fr)
Inventor
Steve W. Martin
Daniele Piergentili
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
Original Assignee
BASF SE
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.)
Filing date
Publication date
Priority to CA002465294A priority Critical patent/CA2465294A1/en
Priority to DE60232006T priority patent/DE60232006D1/de
Priority to JP2003543972A priority patent/JP2005509011A/ja
Priority to IL16154002A priority patent/IL161540A0/xx
Priority to AT02803000T priority patent/ATE428677T1/de
Priority to US10/495,359 priority patent/US7838700B2/en
Application filed by BASF SE filed Critical BASF SE
Priority to EP02803000A priority patent/EP1446372B1/en
Priority to HU0402368A priority patent/HUP0402368A3/hu
Publication of WO2003042132A1 publication Critical patent/WO2003042132A1/en
Priority to IL161540A priority patent/IL161540A/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
    • 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
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/48—Separation; Purification; Stabilisation; Use of additives
    • C07C67/52—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/48—Separation; Purification; Stabilisation; Use of additives
    • C07C67/60—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to chemical modification
    • 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

Definitions

  • This invention relates to a novel process for the recovery of chiral substituted tartaric acid resolving agents from process liquors in a form of sufficient purity to enable their recycle in the corresponding resolution process .
  • optically active amine compounds Chemical processes for the synthesis of optically active amine compounds frequently use optically active organic acid resolving agents to allow the required enantiomer to be preferentially crystallised as a salt with the resolving agent. The required optically active amine can then be regenerated by basification of the salt.
  • WO 01/46148 a process for the manufacture of (-) trans piperidine carbinols is disclosed wherein the racemic piperidine carbinol is contacted with (-)ditoluol tartaric acid, followed by isolation of the crystalline salt and regeneration of the ditoluoltartaric acid by addition of an aqueous inorganic base.
  • optically active tartaric acid derivatives can be recovered from a resolving process for optically active aminopyrrolidones by treatment of the salts with alkalis in water, followed by extraction of the aqueous layer with organic solvents and addition of mineral acids to the aqueous layer.
  • Examples of resolving agents used in such resolution processes include (+) -di-0,0'-toluoyl-(D) -tartaric acid, (-)-di-0,0'- toluoyl- (L) -tartaric acid, (+) -di-0,0'-benzoyl-(D) -tartaric acid, (-) -di-0,0' -benzoyl- (L) -tartaric acid. Examples of such structures are shown in figure 1.
  • R3 H or alkyl
  • R4 H or alkyl
  • Such resolving agents are typically expensive to manufacture or purchase.
  • This invention relates to an efficient method for recovery of the substituted tartaric acid resolving agent from the resolution mother liquor or from the aqueous phase from regeneration of the chiral salt in a form which may be recycled for use in further resolution reactions.
  • mother liquor as used herein means the process liquor from the resolution process as well as the process liquor of the regeneration process.
  • Such process liquors comprise one or more organic solvents in addition to the resolving agent and the optically active amine.
  • organic solvents used for the resolving process are ketones, e.g. acetone, alcohols such as for instance methanol, aromatic hydrocarbons, e.g. toluene, ethers such as for instance tetrahydrofurane or mixtures thereof.
  • the organic solvent is only poorly miscible with water or water immiscible, if not a water miscible solvent needs to be distilled of and replaced by a poorly water miscible or immiscible solvent, e.g. toluene.
  • the mother liquor may be reacted, optionally after solvent exchange, with a suitable base to give a salt of the substituted tartaric acid resolving agent which is dissolved in water to allow separation from organic by-products which may be dissolved in a water immiscible organic solvent .
  • the aqueous phase obtained contains the substituted tartaric acid resolving agent as its salt with the base and is similar in composition to the solution obtained from the regeneration of the optically active amine from its salt with the resolving agent .
  • the base used for neutralisation of the amine salt of the substituted tartaric acid resolving agent may be a hydroxide, carbonate or hydrogen carbonate salt of an alkali or alkaline earth metal or optionally substituted ammonia.
  • the base is sodium or potassium carbonate or hydrogen carbonate or ammonia. More preferably the base is sodium hydrogen carbonate.
  • the base is preferably added in the form of an aqueous solution. The concentration of the base in the solution depends on the type of base used.
  • the co-solvent added to the aqueous solution containing the substituted tartaric acid resolving agent may be any water soluble or partly watersoluble organic solvent, preferably a Ci to l o-alcohol, more preferably 2-butanol.
  • the mineral acid may be any strong acid, preferably sulphuric, phosphoric, hydrochloric, hydrobromic or nitric acid, more preferably hydrochloric acid. The mineral acid is added in amounts sufficient to recover tartaric acid derivative in the form of the free acid.
  • the recovery of the tartaric acid derivatives is typically carried out at 20 to 50°C.
  • the product is filtered off and dried, typically under reduced pressure.
  • the process according to the present invention is particularly advantageous in the recovery of tartaric acid resolving agents from mother liquors in the manufacture of optically pure (+) -l-benzyl-3-hydroxymethyl-4- (-4-fluorophenyl) -1,2,3, 6-tetra- hydropyridine .
  • a particularly advantageous feature of the present invention is the isolation of substituted tartaric acid resolving agent in a crystalline form of suitable purity for reuse in a resolution reaction without additional purification.
  • the substituted tartaric acid resolving agent is typically crystallised as a solvate with the co-solvent used, of a purity in excess of 95% excluding the residual solvent.
  • the optical purity of the substituted tartaric acid resolving agent is not significantly affected by the recovery process .
  • the present invention includes use of such a solvate of the substituted tartaric acid resolving agent in a resolution reaction.
  • (+) -Di-0,0'-toluoyl- (D) -tartaric acid (1270g) was obtained as its 2-butanol solvate, HPLC assay 72%/28% retained solvent, 83% of theory.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
PCT/EP2002/012494 2001-11-14 2002-11-08 Recovery and recycling of chiral tartaric acid resolving agents Ceased WO2003042132A1 (en)

Priority Applications (9)

Application Number Priority Date Filing Date Title
DE60232006T DE60232006D1 (de) 2001-11-14 2002-11-08 Rückgewinnung und recycling chiraler weinsäureverbindungen zur racematspaltung
JP2003543972A JP2005509011A (ja) 2001-11-14 2002-11-08 キラル酒石酸分割剤の回収および再利用
IL16154002A IL161540A0 (en) 2001-11-14 2002-11-08 Recovery and recycling of chiral tartaric acid resolving agents
AT02803000T ATE428677T1 (de) 2001-11-14 2002-11-08 Rückgewinnung und recycling chiraler weinsäureverbindungen zur racematspaltung
US10/495,359 US7838700B2 (en) 2001-11-14 2002-11-08 Recovery and recycling of chiral tartaric acid resolving agents
CA002465294A CA2465294A1 (en) 2001-11-14 2002-11-08 Recovery and recycling of chiral tartaric acid resolving agents
EP02803000A EP1446372B1 (en) 2001-11-14 2002-11-08 Recovery and recycling of chiral tartaric acid resolving agents
HU0402368A HUP0402368A3 (en) 2001-11-14 2002-11-08 Recovery and recycling of chiral tartaric acid resolving agents
IL161540A IL161540A (en) 2001-11-14 2004-04-21 Process for the recovery of substituted tartaric acid resolving agents

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB0127346.5 2001-11-14
GB0127346A GB2382074A (en) 2001-11-14 2001-11-14 Recovery of chiral tartaric acid resolving agents

Publications (1)

Publication Number Publication Date
WO2003042132A1 true WO2003042132A1 (en) 2003-05-22

Family

ID=9925776

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2002/012494 Ceased WO2003042132A1 (en) 2001-11-14 2002-11-08 Recovery and recycling of chiral tartaric acid resolving agents

Country Status (11)

Country Link
US (1) US7838700B2 (enExample)
EP (1) EP1446372B1 (enExample)
JP (1) JP2005509011A (enExample)
AT (1) ATE428677T1 (enExample)
CA (1) CA2465294A1 (enExample)
DE (1) DE60232006D1 (enExample)
ES (1) ES2324772T3 (enExample)
GB (1) GB2382074A (enExample)
HU (1) HUP0402368A3 (enExample)
IL (2) IL161540A0 (enExample)
WO (1) WO2003042132A1 (enExample)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1586551A4 (en) * 2003-01-16 2006-07-26 Toray Finechemicals Co Ltd METHOD FOR OBTAINING OPTICALLY ACTIVE DIACYLTARTIC ACIDS
EP1736462A1 (en) * 2005-06-22 2006-12-27 Sandoz AG Recovery of optically active tartaric acid resolving agents
US12391689B2 (en) 2018-11-16 2025-08-19 Amgen Inc. Synthesis of key intermediate of KRAS G12C inhibitor compound

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES2264378B1 (es) * 2005-05-09 2007-11-01 Ragactives, S.L. Procedimiento para la resolucion de 2-amino-6propilamino-4,5,6,7-tetrahidrobenzotiazol y compuestos intermedios.
MD4504C1 (ro) * 2016-04-13 2018-03-31 Общественное Учреждение "Научно-Практический Институт Садоводства И Пищевых Технологий" Procedeu de obţinere a acidului tartric din tartratul de calciu obţinut din deşeuri vinicole
IL301517A (en) * 2020-10-07 2023-05-01 Amgen Inc A method for preparing the racemate and isolating atropisomers of 7-chloro-6-fluoro-1-(2-isopropyl-4-methylpyridin-3-yl)pyrido[3,2-D]pyrimidine-4,2(1H,3H)-dione
CN112358398A (zh) * 2020-11-19 2021-02-12 山东新华制药股份有限公司 D-(+)-二对甲苯甲酰酒石酸的回收制备方法

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH09176115A (ja) * 1995-12-28 1997-07-08 Koei Chem Co Ltd 光学活性なｎ−ベンジル−３−アミノピロリジンの製造方法

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
HU221921B1 (hu) 1996-07-08 2003-02-28 Richter Gedeon Vegyészeti Gyár Rt. N-benzil-piperidin- és tetrahidropiridinszármazékok és eljárás azok előállítására
CN1173929C (zh) * 1999-10-19 2004-11-03 中国科学院成都有机化学研究所 光学纯肾上腺素类β-激动剂的组合拆分制备法
GB9930577D0 (en) 1999-12-23 2000-02-16 Smithkline Beecham Plc Novel process

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH09176115A (ja) * 1995-12-28 1997-07-08 Koei Chem Co Ltd 光学活性なｎ−ベンジル−３−アミノピロリジンの製造方法

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; SAKAI, TOSHIHITO ET AL: "Preparation of optically-active N-benzyl-3-aminopyrrolidine by resolution with optically-active tartaric acid derivatives and recovery of the resolving agents", XP000223197, retrieved from STN Database accession no. 127:121629 CA *

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1586551A4 (en) * 2003-01-16 2006-07-26 Toray Finechemicals Co Ltd METHOD FOR OBTAINING OPTICALLY ACTIVE DIACYLTARTIC ACIDS
US7358384B2 (en) 2003-01-16 2008-04-15 Toray Fine Chemicals Co., Ltd. Processes for the recovery of optically active diacyltartaric acids
EP1736462A1 (en) * 2005-06-22 2006-12-27 Sandoz AG Recovery of optically active tartaric acid resolving agents
US12391689B2 (en) 2018-11-16 2025-08-19 Amgen Inc. Synthesis of key intermediate of KRAS G12C inhibitor compound
US12391691B2 (en) 2018-11-16 2025-08-19 Amgen Inc. Synthesis of key intermediate of KRAS G12C inhibitor compound

Also Published As

Publication number Publication date
JP2005509011A (ja) 2005-04-07
ES2324772T3 (es) 2009-08-14
GB0127346D0 (en) 2002-01-02
US7838700B2 (en) 2010-11-23
HUP0402368A2 (hu) 2005-03-29
EP1446372A1 (en) 2004-08-18
IL161540A (en) 2011-03-31
CA2465294A1 (en) 2003-05-22
US20050085665A1 (en) 2005-04-21
IL161540A0 (en) 2004-09-27
GB2382074A (en) 2003-05-21
DE60232006D1 (de) 2009-05-28
ATE428677T1 (de) 2009-05-15
EP1446372B1 (en) 2009-04-15
HUP0402368A3 (en) 2008-02-28

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