tert-butyl (2S)-2-[(tert-butoxycarbonyl)amino]-5-isothiocyanatopentanoate -Drug Synthesis Database

【结构式】

【分子编号】30901

【品名】tert-butyl (2S)-2-[(tert-butoxycarbonyl)amino]-5-isothiocyanatopentanoate

【CA登记号】

【分子式】C₁₅H₂₆N₂O₄S

【分子量】330.44852

【元素组成】C 54.52% H 7.93% N 8.48% O 19.37% S 9.7%

与该中间体有关的原料药合成路线共 3 条

合成路线1 合成路线2 合成路线3

合成路线1

该中间体在本合成路线中的序号：(IV)

The fully protection of Nomega-(benzyloxycarbonyl)-L-ornithine (I) by usual methods gives Nomega-(benzyloxycarbonyl)-Nalpha-(tert-butoxycarbonyl)-L-ornithine tert-butyl ester (II), which is selectively deprotected at the omega amino group with H2 over Pd/C yielding the ornithine (III). The reaction of (III) with thiophosgene affords the isothiocyanate (IV), which is treated with hydrazine to afford the aminothiourea (V). Finally, this compound is deprotected with 4M HCl.

参考文献中间体

合成目标

【1】 Ichimori, K.; Stuehr, D.J.; Synthesis and evaluation of new sulfur-containing L-arginine-derived inhibitors of nitric oxide synthase. J Med Chem 1999, 42, 10, 1842.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	30898	(2S)-2-amino-5-[[(benzyloxy)carbonyl]amino]pentanoic acid	C₁₃H₁₈N₂O₄	详情	详情
(II)	30899	tert-butyl (2S)-5-[[(benzyloxy)carbonyl]amino]-2-[(tert-butoxycarbonyl)amino]pentanoate	C₂₂H₃₄N₂O₆	详情	详情
(III)	30900	tert-butyl (2S)-5-amino-2-[(tert-butoxycarbonyl)amino]pentanoate	C₁₄H₂₈N₂O₄	详情	详情
(IV)	30901	tert-butyl (2S)-2-[(tert-butoxycarbonyl)amino]-5-isothiocyanatopentanoate	C₁₅H₂₆N₂O₄S	详情	详情
(V)	30904	tert-butyl (2S)-2-[(tert-butoxycarbonyl)amino]-5-[(hydrazinocarbothioyl)amino]pentanoate	C₁₅H₃₀N₄O₄S	详情	详情

合成路线2

该中间体在本合成路线中的序号：(IV)

The fully protection of Nomega-(benzyloxycarbonyl)-L-ornithine (I) by usual methods gives Nomega-(benzyloxycarbonyl)-Nalpha-(tert-butoxycarbonyl)-L-ornithine tert-butyl ester (II), which is selectively deprotected at the omega amino group with H2 over Pd/C yielding the ornithine (III). The reaction of (III) with thiophosgene affords the isothiocyanate (IV), which is treated with hydroxylamine to afford the hydroxythiourea (V). The methylation of (V) with methyl iodide and NaH affords the S-methyl derivative (VI), which is finally deprotected with 4M HCl.

参考文献中间体

合成目标

【1】 Ichimori, K.; Stuehr, D.J.; Synthesis and evaluation of new sulfur-containing L-arginine-derived inhibitors of nitric oxide synthase. J Med Chem 1999, 42, 10, 1842.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	30898	(2S)-2-amino-5-[[(benzyloxy)carbonyl]amino]pentanoic acid	C₁₃H₁₈N₂O₄	详情	详情
(II)	30899	tert-butyl (2S)-5-[[(benzyloxy)carbonyl]amino]-2-[(tert-butoxycarbonyl)amino]pentanoate	C₂₂H₃₄N₂O₆	详情	详情
(III)	30900	tert-butyl (2S)-5-amino-2-[(tert-butoxycarbonyl)amino]pentanoate	C₁₄H₂₈N₂O₄	详情	详情
(IV)	30901	tert-butyl (2S)-2-[(tert-butoxycarbonyl)amino]-5-isothiocyanatopentanoate	C₁₅H₂₆N₂O₄S	详情	详情
(V)	30902	tert-butyl (2S)-2-[(tert-butoxycarbonyl)amino]-5-[[(hydroxyamino)carbothioyl]amino]pentanoate	C₁₅H₂₉N₃O₅S	详情	详情
(VI)	30903	tert-butyl (2S)-2-[(tert-butoxycarbonyl)amino]-5-[[(Z)-(hydroxyamino)(methylsulfanyl)methylidene]amino]pentanoate	C₁₆H₃₁N₃O₅S	详情	详情

合成路线3

该中间体在本合成路线中的序号：(IV)

参考文献中间体

合成目标

【1】 Ichimori, K.; Stuehr, D.J.; Synthesis and evaluation of new sulfur-containing L-arginine-derived inhibitors of nitric oxide synthase. J Med Chem 1999, 42, 10, 1842.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	30898	(2S)-2-amino-5-[[(benzyloxy)carbonyl]amino]pentanoic acid	C₁₃H₁₈N₂O₄	详情	详情
(II)	30899	tert-butyl (2S)-5-[[(benzyloxy)carbonyl]amino]-2-[(tert-butoxycarbonyl)amino]pentanoate	C₂₂H₃₄N₂O₆	详情	详情
(III)	30900	tert-butyl (2S)-5-amino-2-[(tert-butoxycarbonyl)amino]pentanoate	C₁₄H₂₈N₂O₄	详情	详情
(IV)	30901	tert-butyl (2S)-2-[(tert-butoxycarbonyl)amino]-5-isothiocyanatopentanoate	C₁₅H₂₆N₂O₄S	详情	详情
(V)	30904	tert-butyl (2S)-2-[(tert-butoxycarbonyl)amino]-5-[(hydrazinocarbothioyl)amino]pentanoate	C₁₅H₃₀N₄O₄S	详情	详情
(VI)	30905	tert-butyl (2S)-2-[(tert-butoxycarbonyl)amino]-5-[[(Z)-hydrazino(methylsulfanyl)methylidene]amino]pentanoate	C₁₆H₃₂N₄O₄S	详情	详情

Extended Information