Process for the enzymatic separation of enantiomers of racemic 2-oxotricyclo-2,2,1,03,5-heptan-7-carboxylic acids and esters thereof

• Main Authors: HOLLA, WOLFGANG, BECK, GERHARD
• Format: Patent
• Language: English; French; German
• Published: 01.05.1996
• Edition: 6
• Subjects: ACYCLIC OR CARBOCYCLIC COMPOUNDS; BEER; BIOCHEMISTRY; CHEMISTRY; ENZYMOLOGY; FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIREDCHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERSFROM A RACEMIC MIXTURE; METALLURGY; MICROBIOLOGY; MUTATION OR GENETIC ENGINEERING; ORGANIC CHEMISTRY; PROCESSES USING MICROORGANISMS; SPIRITS; VINEGAR; WINE

Verbindungen der Formel I in denen R¹ die genannten Bedeutungen hat, lassen sich in isomerenreiner Form aus Enantiomeren-Gemischen oder racemischen Gemischen gewinnen, indem man die Verbindung der Formel I in Gegenwart einer Lipase oder Esterase aus Schweineleber, Schweinepankreas, Rinderpankreas oder aus Mikroorganismen wie Candida, Pseudomonas, Mucor, Rhizopus und Aspergillus oder Proteasen aus Bacillus in Gegenwart von Wasser und gegebenenfalls einem Cosolvens umsetzt und die in der erhaltenen Lösung vorliegenden Ester und Säuren voneinander trennt. Process for enzymic resolution (racemate or enantiomer sepn.) of enantiomer or racemic mixts. of oxo-tricyclo-heptane carboxylate cpds. of formula (I) comprises: (a) treating (I) with an enzyme (A) in water and opt. cosolvent and (b) sepg. acid and ester. (A) is a lipase or esterase derived from porcine liver, porcine or bovine pancreas, or from microorganisms such as Candida, Pseudomonas, Mucor, Rhizopus and Aspergillus or a protease from Bacillus. R1 = 1-10C alkyl, 3-10C cycloalkyl, 2-10C alkenyl, 2-10C alkinyl, 3-8C cycloalkenyl (all opt. mono- to tri-substd., by F, Cl, Br, I, CN, COOR, CONH2, R R , NO2, OR, OCOOR, SPh, SMe, SEt, SO2Ph, SO2R, aryl, heteroaryl) or alkyl and alkenyl gps. with 3-10C atoms or alkinyl gps. with 4-10C atoms, 5-10C aryl or 5-10C heteroaryl or N=CR4R5 or C(R6)=CR7R8 or COR9; R = 1-4C alkyl; R2,R3 = H, 1-6C alkyl, 3-10C cycloalkyl, 2-6C alkenyl, 2-6C alkinyl, phenyl, benzyl, benzoyl, or amino-protection gp,; R4,R5 = H or 1-6C alkyl or R4+R5 = alkylene or alkenylene; R6-R8 = H, Me or Et and R9 = H, alkyl or 2-oxo-tricyclo Ä2,2,1,0<3.5>Ühepta-7-carbonyl.