PROCESS FOR PREPARING 3-PYRROLINE-2-CARBOXYLIC ACID DERIVATIVES

    公开(公告)号:CA2261628C

    公开(公告)日:2008-04-22

    申请号:CA2261628

    申请日:1997-07-14

    Applicant: BASF AG

    Abstract: A process is disclosed for preparing 3-pyrroline-2-carboxylic acid derivativ es of formula (I), in which R1 stands for H, C1-C6-alkyl, benzyl, benzyl substituted at the phenyl radical, allyloxycarbonyl, C1-C6- alkyloxycarbonyl, benzyloxycarbonyl, in which the benzyl radical can be substituted by OCH3 radicals, or for C1-C4-alkylcarbonyl; or R1 stand s for an amino acid radical which can be alkylated or acylated at the nitrogen and is linked by the C-terminal; and R2 stands for OH, C1-C4 - alkyloxy, benzyloxy or an N3R4 group, in which R3 and R4 represent independently from each other H, C1-C4-alkyl, benzyl, phenyl or pyridyl, in which the aromatic compounds in R3 and R4 can be substituted by up to three identical or different substituents selected from the group composed of methyl, methoxy, hydroxy, cyano or halogen. According to this process, the sulphonic acid radical is eliminated by means of a base from a compound having the formula (II), in which R1 and R2 have the above meanings and R5 stands for C1-C6-alkyl, benzy l, trifluoromethyl, naphthyl or phenyl optionally substituted by radicals from the group composed of methyl, nitro and halogen.

    RESOLUTION OF RACEMATES OF PRIMARY AND SECONDARY HETEROATOM-SUBSTITUTED AMINES BY ENZYME-CATALYZED ACYLATION

    公开(公告)号:CA2210519C

    公开(公告)日:2006-03-21

    申请号:CA2210519

    申请日:1996-01-20

    Applicant: BASF AG

    Abstract: A process for preparing optically active primary and secondary heteroatom- substituted amines from the corresponding racemates is characterised in that (a) a racemic heteroatom-substituted amine is enantioselectively acylated in the presence of a hydrolase with an ester whose acid component bear a fluorine, nitrogen, phosphorus, oxygen or sulphu r atom next to the carbonyl carbon atom; (b) the mixture of optically active heteroatom-substituted amine and optically active acylated heteroatom-substituted amine is separated in order to produce an enantiomer of the heteroatom-substituted amine; (c) the other enantiomer of the heteroatom-substituted amine is optionally extracted from the acylated heteroatom-substituted amine by amide cleavage.

    35.
    发明专利
    未知

    公开(公告)号:PT801683E

    公开(公告)日:2002-09-30

    申请号:PT96900601

    申请日:1996-01-20

    Applicant: BASF AG

    Abstract: A process for preparing optically active primary and secondary heteroatom-substituted amines from the corresponding racemates, which comprisesa) enantioselective acylation of a racemic heteroatom-substituted amine with an ester whose acid component carries a fluorine, nitrogen, phosphorus, oxygen or sulfur atom in the vicinity of the carbonyl carbon, in the presence of a hydrolase,b) separation of the mixture of optically active heteroatom-substituted amine and optically active acylated heteroatom-substituted amine to obtain one enantiomer of the heteroatom-substituted amine,c) if required isolation of the other enantiomer of the heteroatom-substituted amine from the acylated heteroatom-substituted amine by amide cleavage.

    36.
    发明专利
    未知

    公开(公告)号:PT720655E

    公开(公告)日:2000-04-28

    申请号:PT94928365

    申请日:1994-09-16

    Applicant: BASF AG

    Abstract: PCT No. PCT/EP94/03102 Sec. 371 Date Mar. 11, 1996 Sec. 102(e) Date Mar. 11, 1996 PCT Filed Sep. 16, 1994 PCT Pub. No. WO95/08636 PCT Pub. Date Mar. 30, 1995A process for producing optically active primary and secondary amines from the corresponding racemates is characterised in that (a) a racemic amine is enantioselectively acylated in the presence of a hydrolase with an ester whose acid component bears a fluorine, nitrogen, oxygen or sulphur atom at the proximity of the carbonyl carbon atom; (b) the mixture of optically active amine and optically active acylated amine is separated so that an enantiomer of amine is produced; (c) if desired the other enantiomer of the amine is extracted from the acylated amine by amide cleavage.

    37.
    发明专利
    未知

    公开(公告)号:AT191451T

    公开(公告)日:2000-04-15

    申请号:AT96931783

    申请日:1996-09-09

    Applicant: BASF AG

    Abstract: PCT No. PCT/EP96/03948 Sec. 371 Date Jan. 27, 1998 Sec. 102(e) Date Jan. 27, 1998 PCT Filed Sep. 9, 1996 PCT Pub. No. WO97/10201 PCT Pub. Date Mar. 20, 1997The present invention relates to a process for cleaving optically active amides to carboxylic acids and optically active amines with retention of the center of chirality, wherein the amides are hydrolyzed in the presence of a polyol or of an amino alcohol and of an alkali metal or alkaline earth metal hydroxide.

    METHOD FOR PRODUCING ESTERS FREE OF ENANTIOMERS

    公开(公告)号:CA2274247A1

    公开(公告)日:1998-08-27

    申请号:CA2274247

    申请日:1998-02-09

    Applicant: BASF AG

    Abstract: The invention relates to a method for producing enantiomer-free esters of formula (I) (Ia or Ib), where the substituents represent the following: R1 is a hydrogen or a substituted or unsubstituted C1-C6-alkyl-, C1-C6-alkoxy-, or C1-C6-alkanoyl; R2 and R3 independently of each other are hydrogen or a substituted or unsubstituted C1-C6-alkyl-, C1-C6-alkoxy-, or C1-C6-alkanoyl-, C1-C6-alkylthio-, C1-C6-alkyl sulfinyl or C1-C6-alkyl sulfonyl-; R4 is not equal to R5 and independently of each other they are either hydrogen or an substituted or unsubstituted C1-C6-alkyl-, or together with the hydrogen atoms, to which they are bound, form a substituted or unsubstituted C3-C6-cyclo alkylidene; and R6 is a substituted or unsubstituted aryl-, C1-C20-alkyl-, C3-C20-alkenyl-, C3-C20-alkynyl-, C1-C20-alkoxy-C1-C20-alkyl. The method is characterized in that racemic compounds of the formula (II), in which the substituents R1 to R5 have the meanings given above, are reacted with a lipase or esterase in the presence of vinyl esters of formula (III), where R6 has the meaning given above and R7 represents hydrogen or methyl, to form compounds of formula (I).

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