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【结 构 式】

【分子编号】49914

【品名】tert-butyl (2R)-3-[((1R)-2-[[(benzyloxy)carbonyl]amino]-1-methylethyl)sulfanyl]-2-[(tert-butoxycarbonyl)amino]propanoate

【CA登记号】

【 分 子 式 】C23H36N2O6S

【 分 子 量 】468.61472

【元素组成】C 58.95% H 7.74% N 5.98% O 20.49% S 6.84%

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)

Alkylation of N-Boc-L-cysteine tert-butyl ester (I) with the chiral tosylate (II) gave thioether (III). The N-benzyloxycarbonyl protecting group of (III) was then cleaved by transfer hydrogenolysis using ammonium formate in the presence of Pearlman's catalyst to afford amine (IV). Condensation of this amine with the thioacetimidate (V) gave rise to amidine (VI). The N-Boc and tert-butyl ester protecting groups of (VI) were finally removed by treatment with a solution of HCl in dioxan.

1 Young, R.J.; et al.; Inhibition of inducible nitric oxide synthase by acetamidine derivatives of branched hetero-substituted lysine analogs. 222nd ACS Natl Meet (Aug 26 2001, Chicago) 2001, Abst MEDI 250.
2 Beswick, P.J.; Young, R.J.; Kleanthous, S. (Glaxo Group Ltd.); Nitric oxide synthase inhibitors. EP 1084104; WO 9962875 .
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) 42195 tert-butyl (2R)-2-[(tert-butoxycarbonyl)amino]-3-sulfanylpropanoate C12H23NO4S 详情 详情
(II) 49913 (1S)-2-[[(benzyloxy)carbonyl]amino]-1-methylethyl 4-methylbenzenesulfonate C18H21NO5S 详情 详情
(III) 49914 tert-butyl (2R)-3-[((1R)-2-[[(benzyloxy)carbonyl]amino]-1-methylethyl)sulfanyl]-2-[(tert-butoxycarbonyl)amino]propanoate C23H36N2O6S 详情 详情
(IV) 49915 tert-butyl (2R)-3-[[(1R)-2-amino-1-methylethyl]sulfanyl]-2-[(tert-butoxycarbonyl)amino]propanoate C15H30N2O4S 详情 详情
(V) 42175 1-naphthylmethyl ethanimidothioate C13H13NS 详情 详情
(VI) 49916 tert-butyl (2R)-2-[(tert-butoxycarbonyl)amino]-3-[[(1R)-2-(ethanimidoylamino)-1-methylethyl]sulfanyl]propanoate C17H33N3O4S 详情 详情
Extended Information