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    PRODUCTION OF RACEMIC CARBOXYLIC ACID
    3.
    发明专利
    PRODUCTION OF RACEMIC CARBOXYLIC ACID 失效

    公开(公告)号：JP2000007610A

    公开(公告)日：2000-01-11

    申请号：JP17137698

    申请日：1998-06-18

    Applicant: TORAY INDUSTRIES

    Inventor： IWATA SHIHO ,  SATO HARUYO

    IPC: C07D307/24 ,  C07B55/00 ,  C07B61/00 ,  C07C51/353 ,  C07C57/30

    Abstract: PROBLEM TO BE SOLVED: To produce a racemic carboxylic acid useful as a raw material for manufacture an optically active substance through an optical resolution method which is performed using a small amount of a regent with a simple operation, by mixing a specific optically active carboxylic acid with a specific sulfonyl chloride or the like and heating the mixture in the presence of a base. SOLUTION: (A) An optically active carboxylic acid in which a carboxyl group is bound to an asymmetric carbon [e.g. (R)-tetrahydrofuran-2-carboxylic acid] and (B) (i) a sulfonyl chloride of the formula R1-SO2Cl (R1 is a 1-12C alkyl which is not substituted or substituted with a 1-12C alkyl or the like, or the like) (e.g. benzenesulfonyl chloride) or (ii) a carbonyl chloride of the formula R1-COCl (e.g. benzoyl chloride) are mixed with each other, and the obtained mixture is heated in the presence of (C) a base such as triethylamine preferably at 50-150 deg.C to obtain the objective compound (e.g. tetrahydrofuran-2- carboxylic acid) having a lower optical activity than the component A.

    OPTICALLY ACTIVE AMINO ACID ESTER TARTARIC ACID AMIDE AND ITS PRODUCTION
    4.
    发明专利
    OPTICALLY ACTIVE AMINO ACID ESTER TARTARIC ACID AMIDE AND ITS PRODUCTION 失效

    公开(公告)号：JP2000319244A

    公开(公告)日：2000-11-21

    申请号：JP2000051378

    申请日：2000-02-28

    Applicant: TORAY INDUSTRIES

    Inventor： IWATA SHIHO ,  ONO TAKAE ,  SATO HARUYO

    IPC: C07C235/12 ,  C07B53/00 ,  C07B57/00 ,  C07C231/18

    Abstract: PROBLEM TO BE SOLVED: To obtain a new compound which has a high optical purity and is useful as a raw material for medicines and agrochemicals. SOLUTION: A compound of formula I [R1 is an alkyl, (substituted) phenyl or a (substituted) aralkyl; R2 is an α-amino acid residue; R3 is hydrogen, methyl or methoxy; * means to be optically active], for example, 0, 0'-di p-toluoyl-D- tartaric acid.mono-L-(1,2-dibenzyloxycarbonyl) ethylamide. The compound of formula I can be produced, for example, by reacting an optically active amino acid ester of formula III (for example, L-asparaginic acid dibenzyl ester.para- toluene sulfonic acid salt) with an optically active diacyltartaric acid anhydride of formula IV (for example, 0, 0'-di para-toluoyl-D-tartaric acid anhydride) in a solvent at 0 to 100 deg.C, more preferably at room temperature to 40 deg.C, for 0.1 to 5.0 hr, if necessary, after a neutralization reaction giving a free state.

    PRODUCTION OF AMINO ACID BENZYL ESTER HAVING HIGH OPTICAL PURITY
    5.
    发明专利
    PRODUCTION OF AMINO ACID BENZYL ESTER HAVING HIGH OPTICAL PURITY 失效

    公开(公告)号：JP2000247934A

    公开(公告)日：2000-09-12

    申请号：JP4434099

    申请日：1999-02-23

    Applicant: TORAY INDUSTRIES

    Inventor： ONO TAKAE ,  IWATA SHIHO ,  SATO HARUYO

    IPC: B01J31/02 ,  C07B61/00 ,  C07C227/18 ,  C07C227/32 ,  C07C229/02 ,  C07C229/08 ,  C07C229/24 ,  C07C229/26 ,  C07C231/18 ,  C07C233/47 ,  C07C235/12

    Abstract: PROBLEM TO BE SOLVED: To produce an amino acid benzyl ester useful as a raw material for pharmaceuticals and agrochemicals with a simple operation by reacting an optically active amino acid with a specific benzyl alcohol in the presence of an acid catalyst and a hydrazine compound. SOLUTION: An optically active amino acid (e.g. a neutral α-amino acid such as alanine, an acidic α-amino acid such as aspartic acid, a basic α-amino acid such as lysine and a β-amino acid such as 3-aminobutyric acid) is made to react with a benzyl alcohol compound of formula I (R1 and R2 are each H, a lower alkyl, a lower alkoxyl or a halogen) (e.g. 4-methylbenzyl alcohol) in the presence of an acid catalyst (e.g. p-toluenesulfonic acid) and a hydrazine compound [preferably an aromatic hydrazine, especially hydrazine of formula II (R3 and R4 are each H, a lower alkyl, a halogen or nitro; (n) is 0-3), concretely phenylhydrazine, etc.]. The reaction is preferably carried out at 60-130 deg.C in the absence of oxygen.

    PRODUCTION OF CARBOXYLIC ACID OR ITS ESTER
    6.
    发明专利
    PRODUCTION OF CARBOXYLIC ACID OR ITS ESTER 失效

    公开(公告)号：JPH0971576A

    公开(公告)日：1997-03-18

    申请号：JP22894295

    申请日：1995-09-06

    Applicant: TORAY INDUSTRIES

    Inventor： NAKAI SAKIE ,  SATOU HARUYO ,  IWATA SHIHO

    IPC: C07D307/24 ,  C07C27/02 ,  C07C51/02 ,  C07C67/14 ,  C07D309/08

    Abstract: PROBLEM TO BE SOLVED: To isolate carboxylic acid or its ester which is useful as an intermediate for medicines or as a starting material for liquid crystal in high purity and high yield by bringing a salt of carboxylic acid into contact with a hydrogen halide to effect salt dissolution in a substantially water-free (anhydrous) organic solvent. SOLUTION: Preferably, in an alcohol solvent or in at least one of organic solvent selected from ethers, halogenated hydrocarbons and hydrocarbons containing an alcohol, (A) a salt of carboxylic acid (a salt of tetrahydrofrancarboxylic acid or tetrahydropyranecarboxylic acid with an alkali metal ion, an alkaline earth metal ion or an organic amine) is brought into contact with (B) a hydrogen halide such as hydrogen chloride, hydrogen bromide or hydrogen iodide to dissolve the salt to give the objective carboxylic acid or its ester. The component A is preferably brought into contact with the component B at 0 deg.C-50 deg.C. The amount of the organic solvent is preferably 0.5-20 times, more preferably 1-10 times the component A in weight.

    PRODUCTION OF OPTICALLY ACTIVE CARBOXYLIC ACID
    7.
    发明专利
    PRODUCTION OF OPTICALLY ACTIVE CARBOXYLIC ACID 失效

    公开(公告)号：JPH09143101A

    公开(公告)日：1997-06-03

    申请号：JP30545395

    申请日：1995-11-24

    Applicant: TORAY INDUSTRIES

    Inventor： NAKAI SAKIE ,  SATOU HARUYO ,  IWATA SHIHO

    IPC: C07D307/24 ,  C07B57/00 ,  C07B63/00 ,  C07D309/08

    Abstract: PROBLEM TO BE SOLVED: To obtain an optically active carboxylic acid by optical resolution of the diastereomer salt from the corresponding racemic carboxylic acid by use of an optical resolution agent. SOLUTION: This optically active carboxylic acid is obtained by the following processes: (A) a racemic carboxylic acid is mixed with an optical resolution agent in an organic solvent followed by separation of the corresponding optically active carboxylic acid and the diastereomer salt of the optical resolution agent in the form of crystal by solid-liquid separation; (B) the optically antipodal, carboxylic acid and the optical resolution agent left in the organic solvent mother liquor after the solid-liquid separation are brought into contact with a chlorinating agent in the coexistence of an alcohol to separate and recover the optically antipodal carboxylic ester and optical resolution agent hydrochloride crystal from the optical resolution agent hydrochloride; (C) racemization and hydrolysis process where the optically antipodal carboxylic ester left in the mother liquor is recovered as racemic carboxylic acid; (D) the optical resolution agent is recovered as isolated state from the optical resolution agent hydrochloride; and (E) both the racemic carboxylic acid and optical resolution agent recovered is recycled to the optical resolution process A.

    RACEMIC ALIPHATIC HETEROCYCLIC CARBOXYLIC ACID ESTER, AND PRODUCTION OF RACEMIC ALIPHATIC HETEROCYCLIC CARBOXYLIC ACID
    8.
    发明专利
    RACEMIC ALIPHATIC HETEROCYCLIC CARBOXYLIC ACID ESTER, AND PRODUCTION OF RACEMIC ALIPHATIC HETEROCYCLIC CARBOXYLIC ACID 失效

    公开(公告)号：JPH08104686A

    公开(公告)日：1996-04-23

    申请号：JP13462395

    申请日：1995-06-01

    Applicant: TORAY INDUSTRIES

    Inventor： NAKAI SAKIE ,  SATOU HARUYO ,  IWATA SHIHO

    IPC: C07D307/24 ,  C07B55/00 ,  C07B61/00 ,  C07D309/08

    Abstract: PURPOSE: To obtain the subject compound in a short time and in a high yield under mild conditions by racemizing an optically active aliphatic heterocyclic carboxylic acid ester in the coexistence of as a base. CONSTITUTION: An optically active aliphatic heterocyclic carboxylic acid ester of the formula (R is 1-5C alkyl; n is 1,2) (e.g. optically active tetrahydrofuran-2- carboxylic acid ester) is racemized in the coexistence of a base (preferably an alkali metal alkoxide, alkali metal hydride, alkali metal amide) to obtain the objective compound. The catalyst is preferably used in an amount of 0.01-35mol% based on the compound of formula. The racemization reaction is preferably performed at 0-65 deg.C under an anhydrous condition. The reaction time is usually 0.1-30hr. A racemic aliphatic heterocyclic carboxylic acid is obtained by hydrolyzing the objective compound.

    PRODUCTION OF RACEMIC CARBOXYLIC ACID
    9.
    发明专利
    PRODUCTION OF RACEMIC CARBOXYLIC ACID 失效

    公开(公告)号：JP2000016962A

    公开(公告)日：2000-01-18

    申请号：JP18451398

    申请日：1998-06-30

    Applicant: TORAY INDUSTRIES

    Inventor： IWATA SHIHO ,  SATO HARUYO

    IPC: C07D307/24 ,  C07B55/00 ,  C07B61/00 ,  C07C51/353 ,  C07C53/00 ,  C07C57/30

    Abstract: PROBLEM TO BE SOLVED: To provide a racemic carboxylic acid suitable for producing an optically active carboxylic acid useful for a medicine, etc., by a simple operation with small amounts of reagents from an optical isomer recovered by an optical resolution method by mixing a specific optically active carboxylic acid with a prescribed acid anhydride and heating the mixture in the presence of a base. SOLUTION: (A) An optically active carboxylic acid containing a carboxyl group bonded to an asymmetric carbon atom [e.g. (R)-tetrahydrofuran-2- carboxylic acid or the like] is reacted with (B) an acid anhydride of the formula (R1-CO)2O (R1 is a 1-12C alkyl which is not substituted or substituted with a 1-12C alkyl or the like) (e.g. acetic anhydride or the like) in the ratio of preferably 0.01-0.4 equivalent of the component B based on the component A and heated in the presence of (C) a base being a tertiary amine such as preferably triethylamine or the like favorably at 50-150 deg.C generally for 1-20 hours to give the objective compound (e.g. tetrahydrofuran-2-carboxylic acid or the like).

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