(2S)-4-[(2-aminoethyl)sulfanyl]-2-[(tert-butoxycarbonyl)amino]butyric acid -Drug Synthesis Database

【结构式】

【分子编号】42174

【品名】(2S)-4-[(2-aminoethyl)sulfanyl]-2-[(tert-butoxycarbonyl)amino]butyric acid

【CA登记号】

【分子式】C₁₁H₂₂N₂O₄S

【分子量】278.37276

【元素组成】C 47.46% H 7.97% N 10.06% O 22.99% S 11.52%

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：(VII)

Alternatively, amino acid (III) was protected as the N-Boc derivative (VI), and the benzyloxycarbonyl group was then cleaved by transfer hydrogenolysis employing formic acid and palladium catalyst. The resulting amine (VII) was converted to amidine (IX) by reaction with S-(1-naphthylmethyl)thioacetimidate hydrochloride (VIII). The Boc protecting group of (VIII) was finally removed by acidic treatment.

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 hetero-substituted lysine and homolysine. Bioorg Med Chem Lett 2000, 10, 6, 597.
【2】 Beams, R.M.; Frend, A.J.; Drysdale, M.J.; Franzman, K.W.; Hodson, H.F.; Rees, D.D.; Knowles, R.G.; Sawyer, D.A. (Glaxo Wellcome plc); Nitric oxide synthase inhibitors. EP 0958277; JP 2000504041; WO 9830537 .

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(III)	42171	(2S)-2-amino-4-[(2-[[(benzyloxy)carbonyl]amino]ethyl)sulfanyl]butyric acid	C₁₄H₂₀N₂O₄S	详情	详情
(VI)	42173	(2S)-4-[(2-[[(benzyloxy)carbonyl]amino]ethyl)sulfanyl]-2-[(tert-butoxycarbonyl)amino]butyric acid	C₁₉H₂₈N₂O₆S	详情	详情
(VII)	42174	(2S)-4-[(2-aminoethyl)sulfanyl]-2-[(tert-butoxycarbonyl)amino]butyric acid	C₁₁H₂₂N₂O₄S	详情	详情
(VIII)	42175	1-naphthylmethyl ethanimidothioate	C₁₃H₁₃NS	详情	详情
(IX)	42176	(2S)-2-[(tert-butoxycarbonyl)amino]-4-[[2-(ethanimidoylamino)ethyl]sulfanyl]butyric acid	C₁₃H₂₅N₃O₄S	详情	详情

Extended Information