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【结 构 式】

【分子编号】39362

【品名】(3S)-3-amino-N-(1,3-benzodioxol-5-ylmethyl)-4-cyclohexyl-2-hydroxybutanamide

【CA登记号】

【 分 子 式 】C18H26N2O4

【 分 子 量 】334.41552

【元素组成】C 64.65% H 7.84% N 8.38% O 19.14%

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:(XXIII

Cyclohexylalanine (XIV) was protected as the Boc derivative (XV) and then coupled with N,O-dimethylhydroxylamine to produce the Weinreb amide (XVI). Reduction of (XVI) with LiAlH4 at -78 C gave aldehyde (XVII) and subsequent addition of tert-butyl isonitrile furnished hydroxy amide (XVIII). After acid hydrolysis of (XVIII), amino acid (XIX) was protected as the N-Boc derivative (XX). This was coupled with benzodioxolylmethyl amine (XXI) yielding amide (XXII). Acid deprotection of the Boc group of (XXII) gave (XXIII), which was further coupled with dipeptide (VII) to generate tripeptide amide (XXIV). Following hydrogenolytic deprotection of the N-nitro group of (XXIV), Swern oxidation of the alcohol group gave rise to the title compound.

1 Semple, J.E.; et al.; Novel, potent, and selective factor Xa inhibitors featuring a hydrophobic P1-ketoamide moiety. 219th ACS Natl Meet (March 26 2000, San Francisco) 2000, Abst MEDI 193.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(XXIII 39362 (3S)-3-amino-N-(1,3-benzodioxol-5-ylmethyl)-4-cyclohexyl-2-hydroxybutanamide C18H26N2O4 详情 详情
(VII) 39350   C16H24N6O7S 详情 详情
(XIV) 39357 (2S)-2-amino-3-cyclohexylpropionic acid; L-Cyclohexylalanine 27527-05-5 C9H17NO2 详情 详情
(XV) 23050 (2S)-2-[(tert-butoxycarbonyl)amino]-3-cyclohexylpropionic acid C14H25NO4 详情 详情
(XVI) 39358 tert-butyl (1S)-1-(cyclohexylmethyl)-2-[methoxy(methyl)amino]-2-oxoethylcarbamate C16H30N2O4 详情 详情
(XVII) 15853 tert-butyl N-[(1S)-2-cyclohexyl-1-formylethyl]carbamate C14H25NO3 详情 详情
(XVIII) 39359 tert-butyl (1S)-3-(tert-butylamino)-1-(cyclohexylmethyl)-2-hydroxy-3-oxopropylcarbamate C19H36N2O4 详情 详情
(XIX) 12329 (2R,3S)-3-Amino-4-cyclohexyl-2-hydroxybutyric acid C10H19NO3 详情 详情
(XX) 39360 (3S)-3-[(tert-butoxycarbonyl)amino]-4-cyclohexyl-2-hydroxybutyric acid C15H27NO5 详情 详情
(XXI) 33669 1,3-benzodioxol-5-ylmethylamine; 1,3-benzodioxol-5-ylmethanamine; 3,4-Methylendioxybenzylamine 2620-50-0 C8H9NO2 详情 详情
(XXII) 39361 tert-butyl (1S)-3-[(1,3-benzodioxol-5-ylmethyl)amino]-1-(cyclohexylmethyl)-2-hydroxy-3-oxopropylcarbamate C23H34N2O6 详情 详情
(XXIV) 39363   C34H48N8O10S 详情 详情
Extended Information