(2S)-2-amino-4-[(2-[[(benzyloxy)carbonyl]amino]ethyl)sulfanyl]butyric acid -Drug Synthesis Database

【结构式】

【分子编号】42171

【品名】(2S)-2-amino-4-[(2-[[(benzyloxy)carbonyl]amino]ethyl)sulfanyl]butyric acid

【CA登记号】

【分子式】C₁₄H₂₀N₂O₄S

【分子量】312.38988

【元素组成】C 53.83% H 6.45% N 8.97% O 20.49% S 10.26%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(III)

Reductive cleavage of L-homocystine (I) with sodium in liquid ammonia produced homocysteine, which was subsequently alkylated with 2-(N-benzyloxycarbonyl-amino)ethyl tosylate (II) to afford thioether (III). The benzyloxycarbonyl protecting group of (III) was cleaved with HBr to give diamine (IV). Finally, condensation with ethyl acetimidate (V) furnished the target amidine.

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	CAS号	分子式	供应商	用于合成
(I)	42169	(2S)-2-amino-4-[[(3S)-3-amino-3-carboxypropyl]disulfanyl]butyric acid		C₈H₁₆N₂O₄S₂	详情	详情
(II)	42170	2-[[(benzyloxy)carbonyl]amino]ethyl 4-methylbenzenesulfonate		C₁₇H₁₉NO₅S	详情	详情
(III)	42171	(2S)-2-amino-4-[(2-[[(benzyloxy)carbonyl]amino]ethyl)sulfanyl]butyric acid		C₁₄H₂₀N₂O₄S	详情	详情
(IV)	42172	(2S)-2-amino-4-[(2-aminoethyl)sulfanyl]butyric acid		C₆H₁₄N₂O₂S	详情	详情
(V)	12831	ethyl ethanimidoate	1000-84-6	C₄H₉NO	详情	详情

合成路线2

该中间体在本合成路线中的序号：(III)

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