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【结 构 式】

【分子编号】52878

【品名】1-(tert-butyl) 2-ethyl (2R,4R)-4-[(methylsulfonyl)oxy]-1,2-pyrrolidinedicarboxylate

【CA登记号】

【 分 子 式 】C13H23NO7S

【 分 子 量 】337.39416

【元素组成】C 46.28% H 6.87% N 4.15% O 33.19% S 9.5%

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:(III)

The protected amino acid precursor (VI) was synthesized as follows. cis-4-Hydroxy-D-proline (I) was esterified with EtOH/HCl and subsequently protected as the N-Boc derivative (II). Treatment of (II) with methanesulfonyl chloride and triethylamine afforded the corresponding mesylate (III), which was displaced with NaCN in DMSO to produce nitrile (IV). Reduction of nitrile (IV) to the primary amine (V) was effected by catalytic hydrogenation over PtO2. Acylation of the free amino group of (V) with Boc2O, followed by basic hydrolysis of the ethyl ester, furnished the di-Boc-protected (aminomethyl)proline (VI).

1 Renau, T.E.; et al.; Conformationally restricted analogs of efflux pump inhibitors that potentiate the activity of levofloxacin in Pseudomonas aeruginosa. 41st Intersci Conf Antimicrob Agents Chemother (Dec 16 2001, Chicago) 2001, Abst F-341.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 27400 (2R,4R)-4-hydroxy-2-pyrrolidinecarboxylic acid C5H9NO3 详情 详情
(II) 52877 1-(tert-butyl) 2-ethyl (2R,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate C12H21NO5 详情 详情
(III) 52878 1-(tert-butyl) 2-ethyl (2R,4R)-4-[(methylsulfonyl)oxy]-1,2-pyrrolidinedicarboxylate C13H23NO7S 详情 详情
(IV) 52879 1-(tert-butyl) 2-ethyl (2R,4S)-4-cyano-1,2-pyrrolidinedicarboxylate C13H20N2O4 详情 详情
(V) 52880 1-(tert-butyl) 2-ethyl (2R,4R)-4-(aminomethyl)-1,2-pyrrolidinedicarboxylate C13H24N2O4 详情 详情
(VI) 52881 (2R,4R)-1-(tert-butoxycarbonyl)-4-{[(tert-butoxycarbonyl)amino]methyl}-2-pyrrolidinecarboxylic acid C16H28N2O6 详情 详情
Extended Information