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    • 65. 发明专利
      PL319775A1 NOVEL EFFECTIVE AND HIGHLY ENANTIOSEL; ECTIVE METHOD OF OBTAINING ENANTIOMETRICALLY PURE CYCLOPENTANE BETA-AMINO ACID 未知
    • NOVEL EFFECTIVE AND HIGHLY ENANTIOSEL; ECTIVE METHOD OF OBTAINING ENANTIOMETRICALLY PURE CYCLOPENTANE BETA-AMINO ACID
    • PL319775A1
    • 1997-11-10
    • PL31977597
    • 1997-04-30
    • BAYER AG
    • MITTENDORF JOACHIM
    • B01J31/12 , C07B61/00 , C07C69/74 , C07C227/32 , C07C229/48 , C07C271/24 , C07C227/12
    • Preparation of enantiomerically pure cyclopentane beta -amino acid compounds of formula (I) comprises (a) reaction of meso-dicarboxylic acid anhydride of formula (II) with an alkenol of formula (III) in the presence of an equimolar amount of a chiral base and in an inert solvent to give an enantiomerically pure ester of formula (IV); (b) conversion of (IV) into the enantiomerically pure acid (IVa) of formula (IV; E = H); (c) conversion to the azide by (1) Curtius rearrangement by reacting (IVa) with an azide of formula (R O)2P(O)N3 (V) in the presence of a base and in an inert solvent, or (2) activation of carboxyl group of (IVa) and reaction with an alkali azide or trialkylsilylazide; (d) reaction to the isocyanate of formula (VI); (e) reaction with (III) to give the diester of formula (VII); and (f) cleavage of the urethane and ester functions in an inert solvent in the presence of a Pd catalyst and/or a phosphine and a nucleophilic reagent. A, D = H, halo, OH or 1-8C alkyl (optionally mono- or di-substituted by halo, OH, Ph, benzyloxy, COOH, 1-6C alkoxy, 1-6C acyl, 1-6C alkoxycarbonyl or NR R ); or A and D together form =CR R ; E = chiral amine base; R , R = H, halo, 1-8C alkyl, 1-8C alkoxy, 1-8C hydroxyacyl, benzyl or Ph; R , R = H, 1-5C alkyl or Ph, (optionally mono- to tri- substituted by halo, CN, OCF3, NO2, CF3, 1-6C alkyl or 1-6C alkoxy); R = as for R , or 5-7 membered heteroaromatic with 3 heteroatoms from S, N and/or O; R = Ph or 1-6C alkyl; R , R = H, Ph or 1-6C alkyl. The enantiomer-pure compounds (IV), (IVa) and (VII) are new.
    • 基本信息 添加关注 加入工作空间 PDF全文 PDF下载 全文下载 相似专利 双屏查看 权利要求书 说明书全文 Espacenet 法律信息 同族专利 专利引用
    • 67. 发明专利
      BR9506509A  未知
    • BR9506509A
    • 1997-09-09
    • BR9506509
    • 1995-01-09
    • BAYER AG
    • MITTENDORF JOACHIM , AROLD HERMANN , FEY PETER , MATZKE MICHAEL , MILITZER HANS-CHRISTIAN , MOHRS KLAUS-HELMUT
    • C07D307/93 , C07C61/35 , C07C67/08 , C07C69/608 , C07C69/74 , C07C69/753 , C07C69/757 , C07C227/32 , C07C229/28 , C07C229/48 , C07C231/02 , C07C231/18 , C07C233/00 , C07C233/58 , C07C255/14 , C07C271/24 , C07D453/00 , C07D453/04 , C07F7/08
    • Prepn. of enantiomerically pure cyclopentane- or cyclopentene- beta -aminoacids of formula (I) comprises:(a) converting a meso-cyclopentane- or cyclopentene dicarboxylic anhydride of formula (II) into an enantiomerically pure monoester of formula (IVa) via enantiomerically pure salt of formula (IV), by asymmetric alcoholysis with an alcohol of formula (III) in a solvent in presence of an equimolar amt. of a chiral amine base in pure enantiomer form;(b) activating the free carboxy function then reacting with liq. ammonia to give the enantiomerically pure amide of formula (V);(c) cleaving the ester residue R in an inert solvent in presence of a nucleophilic auxiliary, by enzymatic methods or in presence of a palladium catalyst to give the acid or salt of formula (VI);(d) carrying out Hoffmann rearrangement with alkali(ne earth) metal hypochlorite in aq. alkali(ne earth) metal hydroxide soln.;(e) blocking the free amino gp. in soln. using a conventional amino-protecting gp., isolating the protected cpds. and cleaving the protecting gp. to give the pure enantiomer of (I). A,L = H;D, E = H, halo, OH or 1-8C alkyl,etc.; or D+E = =CR R , =N-OH, =O or =S; or A+D or E+L = additional bond;R , R = H, halo, 1-8C alkyl, 1-8C alkoxy,etc.; R = H, amino-protecting gp., 1-8C alkyl (opt. substd. by 1 or 2 of OH, CHO up to 6C acyl, phenyl and benzoyl, where phenyl and benzoyl are themselves opt. substd. by 1 or 2 of halo, NO2, CN and 1-6C alkyl),etc.;R =H or 1-8C alkyl (opt. substd. by phenyl); or R +R = =CHR ;R = H or 1-8C alkyl (opt. substd. by halo, OH,etc.;T = O, S or NH; R = H, 1-8C alkyl (opt. substd. by 1-3 of OH, halo,etc.), phenyl (opt. substd. by 1-3 of OH, halo, NO2,etc.);or if T = e.g. NH, R = 2-5C alkyl or 2-5C alkenyl (opt. substd. by CN, SiMe3, Ph or CCl3);V = chiral amine base;X = H, alkali metal or alkaline earth metal. Enantiomerically pure cpds. (IV), (IVa) and (V) are new.
    • 基本信息 添加关注 加入工作空间 PDF全文 PDF下载 全文下载 相似专利 双屏查看 权利要求书 说明书全文 Espacenet 法律信息 同族专利 专利引用
    • 68. 发明专利
      HU9700831D0 NEW, EFFECTUAL AND STRONGLY ENANTIOSELECTIVE PROCESS FOR PRODUCING PURE ENANTIOMERE CYCLOPENTANE-BETA-AMINO-ACIDS 未知
    • NEW, EFFECTUAL AND STRONGLY ENANTIOSELECTIVE PROCESS FOR PRODUCING PURE ENANTIOMERE CYCLOPENTANE-BETA-AMINO-ACIDS
    • HU9700831D0
    • 1997-06-30
    • HU9700831
    • 1997-04-30
    • BAYER AG
    • MITTENDORF JOACHIM
    • B01J31/12 , C07B61/00 , C07C69/74 , C07C227/32 , C07C229/48 , C07C271/24
    • Preparation of enantiomerically pure cyclopentane beta -amino acid compounds of formula (I) comprises (a) reaction of meso-dicarboxylic acid anhydride of formula (II) with an alkenol of formula (III) in the presence of an equimolar amount of a chiral base and in an inert solvent to give an enantiomerically pure ester of formula (IV); (b) conversion of (IV) into the enantiomerically pure acid (IVa) of formula (IV; E = H); (c) conversion to the azide by (1) Curtius rearrangement by reacting (IVa) with an azide of formula (R O)2P(O)N3 (V) in the presence of a base and in an inert solvent, or (2) activation of carboxyl group of (IVa) and reaction with an alkali azide or trialkylsilylazide; (d) reaction to the isocyanate of formula (VI); (e) reaction with (III) to give the diester of formula (VII); and (f) cleavage of the urethane and ester functions in an inert solvent in the presence of a Pd catalyst and/or a phosphine and a nucleophilic reagent. A, D = H, halo, OH or 1-8C alkyl (optionally mono- or di-substituted by halo, OH, Ph, benzyloxy, COOH, 1-6C alkoxy, 1-6C acyl, 1-6C alkoxycarbonyl or NR R ); or A and D together form =CR R ; E = chiral amine base; R , R = H, halo, 1-8C alkyl, 1-8C alkoxy, 1-8C hydroxyacyl, benzyl or Ph; R , R = H, 1-5C alkyl or Ph, (optionally mono- to tri- substituted by halo, CN, OCF3, NO2, CF3, 1-6C alkyl or 1-6C alkoxy); R = as for R , or 5-7 membered heteroaromatic with 3 heteroatoms from S, N and/or O; R = Ph or 1-6C alkyl; R , R = H, Ph or 1-6C alkyl. The enantiomer-pure compounds (IV), (IVa) and (VII) are new.
    • 基本信息 添加关注 加入工作空间 PDF全文 PDF下载 全文下载 相似专利 双屏查看 权利要求书 说明书全文 Espacenet 法律信息 同族专利 专利引用
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