tert-butyl (2R)-3-[((1R)-2-[[(benzyloxy)carbonyl]amino]-1-methylethyl)sulfanyl]-2-[(tert-butoxycarbonyl)amino]propanoate -Drug Synthesis Database

【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.

参考文献中间体

合成目标

【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	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