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【结 构 式】

【分子编号】30640

【品名】benzyl (1S)-1-benzyl-2-[(1R)-5-bromo-1-methyl-1,3-dihydro-2H-isoindol-2-yl]-2-oxoethylcarbamate

【CA登记号】

【 分 子 式 】C26H25BrN2O3

【 分 子 量 】493.40018

【元素组成】C 63.29% H 5.11% Br 16.19% N 5.68% O 9.73%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(XXVI)

The chiral indolines (XIX) and (XX) have been obtained as follows: The condensation of racemic 5-bromo-2-methylindoline (XXIII) with N-(benzyloxycarbonyl)-L-phenylalanine (XXIV) by means of DIC and triethylamine in THF gives the diastereomeric mixture of indolines (XXV), which is separated by column chromatography, yielding the pure enantiomer (XXVI). The cleavage of (XXVI) with 6N HCl affords 5-bromo-1(R)-methylisoindoline (XXVII), which is treated with trityl chloride and triethylamine in dichloromethane to give indoline (XIX), or with benzyl chloroformate and triethylamine to give indoline (XX).

1 Castañer, J.; Rabasseda, X.; Graul, A.; T-3811ME. Drugs Fut 1999, 24, 12, 1324.
2 Todo, Y.; Hayashi, K.; Takahata, M.; Watanabe, Y.; Narita, H. (Toyama Chemical Co., Ltd.); Quinolonecarboxylic acid derivs. or salts thereof.. EP 0882725; US 6025370; WO 9729102 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(XIX) 30634 (1R)-5-bromo-1-methyl-2-trityl-2,3-dihydro-1H-isoindole C28H24BrN 详情 详情
(XX) 30635 benzyl (1R)-5-bromo-1-methyl-1,3-dihydro-2H-isoindole-2-carboxylate C17H16BrNO2 详情 详情
(XXIII) 30638 5-bromo-1-methylisoindoline C9H10BrN 详情 详情
(XXIV) 14505 (2S)-2-[[(benzyloxy)carbonyl]amino]-3-phenylpropionic acid; N-Carbobenzyloxy-L-phenylalanine; N-Cbz-L-Phenylalanine 1161-13-3 C17H17NO4 详情 详情
(XXV) 30639 benzyl (1S)-1-benzyl-2-(5-bromo-1-methyl-1,3-dihydro-2H-isoindol-2-yl)-2-oxoethylcarbamate C26H25BrN2O3 详情 详情
(XXVI) 30640 benzyl (1S)-1-benzyl-2-[(1R)-5-bromo-1-methyl-1,3-dihydro-2H-isoindol-2-yl]-2-oxoethylcarbamate C26H25BrN2O3 详情 详情
(XXVII) 30641 (1R)-5-bromo-1-methyl-2,3-dihydro-1H-isoindole C9H10BrN 详情 详情
Extended Information