benzyl (1S)-1-[cyano(hydroxy)methyl]-2-methylpropylcarbamate -Drug Synthesis Database

【结构式】

【分子编号】62768

【品名】benzyl (1S)-1-[cyano(hydroxy)methyl]-2-methylpropylcarbamate

【CA登记号】

【分子式】C₁₄H₁₈N₂O₃

【分子量】262.3086

【元素组成】C 64.11% H 6.92% N 10.68% O 18.3%

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：(I)

N-Cbz-L-Valinal cyanohydrin (I) is converted into imidate (II) and then condensed with 2-aminophenol (III) to afford benzoxazole (IV). Removal of the N-Cbz group of (IV) with H2 and Pd/C provides amine (V), which is then coupled to N-Cbz-valyl proline (VI), yielding the dipeptide amide (VII). After hydrogenolysis of the N-Cbz protecting group of (VII), the free amine (VIII) is coupled to the acid fragment (IX) by means of EDC/pyridine to furnish (X).

参考文献中间体

合成目标

【1】 Sato, F.; Inoue, Y.; Omodani, T.; Imano, K.; Okazaki, H.; Takemura, T.; Komiya, M.; Design and synthesis of peptide-based carboxylic acid-containing transition-state inhibitors of human neutrophil elastase. Bioorg Med Chem Lett 2002, 12, 4, 551.

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)	62768	benzyl (1S)-1-[cyano(hydroxy)methyl]-2-methylpropylcarbamate		C₁₄H₁₈N₂O₃	详情	详情
(II)	62769	ethyl (3S)-3-{[(benzyloxy)carbonyl]amino}-2-hydroxy-4-methylpentanimidoate		C₁₆H₂₄N₂O₄	详情	详情
(III)	18663	o-aminophenol; 2-aminophenol	95-55-6	C₆H₇NO	详情	详情
(IV)	62770	benzyl (1S)-1-[1,3-benzoxazol-2-yl(hydroxy)methyl]-2-methylpropylcarbamate		C₂₀H₂₂N₂O₄	详情	详情
(V)	62771	(2S)-2-amino-1-(1,3-benzoxazol-2-yl)-3-methyl-1-butanol		C₁₂H₁₆N₂O₂	详情	详情
(VI)	22787	(2S)-1-((2S)-2-[[(benzyloxy)carbonyl]amino]-3-methylbutanoyl)-2-pyrrolidinecarboxylic acid		C₁₈H₂₄N₂O₅	详情	详情
(VII)	62772	benzyl (1S)-1-({(2S)-2-[({(1S)-1-[1,3-benzoxazol-2-yl(hydroxy)methyl]-2-methylpropyl}amino)carbonyl]pyrrolidinyl}carbonyl)-2-methylpropylcarbamate		C₃₀H₃₈N₄O₆	详情	详情
(VIII)	55792	(2S)-1-[(2S)-2-amino-3-methylbutanoyl]-N-{(1S)-1-[(S)-1,3-benzoxazol-2-yl(hydroxy)methyl]-2-methylpropyl}-2-pyrrolidinecarboxamide		C₂₂H₃₂N₄O₄	详情	详情
(IX)	62773	2-({4-[2-(tert-butoxy)-2-oxoethoxy]benzoyl}amino)acetic acid		C₁₅H₁₉NO₆	详情	详情
(X)	62774	tert-butyl 2-(4-{[(2-{[(1S)-1-({(2S)-2-[({(1S)-1-[1,3-benzoxazol-2-yl(hydroxy)methyl]-2-methylpropyl}amino)carbonyl]pyrrolidinyl}carbonyl)-2-methylpropyl]amino}-2-oxoethyl)amino]carbonyl}phenoxy)acetate		C₃₇H₄₉N₅O₉	详情	详情

Extended Information