methyl 4-({2-[{[(1,1-dimethylethyl)oxy]carbonyl}(methyl)amino]-4-methylpentanoyl}amino)-2-({[(phenylmethyl)oxy]carbonyl}amino)butanoate -Drug Synthesis Database

【结构式】

【分子编号】64986

【品名】methyl 4-({2-[{[(1,1-dimethylethyl)oxy]carbonyl}(methyl)amino]-4-methylpentanoyl}amino)-2-({[(phenylmethyl)oxy]carbonyl}amino)butanoate

【CA登记号】

【分子式】C₂₅H₃₉N₃O₇

【分子量】493.60068

【元素组成】C 60.83% H 7.96% N 8.51% O 22.69%

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：(IV)

2-N-(Benzyloxycarbonyl)-L-2,4-diaminobutyric acid (I) is esterified by means of SOCl2 in MeOH to afford the corresponding methyl ester (II). Subsequent coupling of (II) with N-Boc-N-methyl-L-leucine (III) leads to dipeptide (IV). The N-benzyloxycarbonyl group of (IV) is removed by catalytic hydrogenation over Pd/C to furnish amine (V), which is further acylated with N-benzyloxycarbonyl-L-proline succinimidyl ester (VI) yielding tripeptide (VII). Then, acidic cleavage of the N-Boc protecting group (VII) produces (VIII).

参考文献中间体

合成目标

【1】 Lee, W.-C.; Scott, D.; Cornebise, M.; Petter, R. (Biogen Idec Inc.); Cell adhesion inhibitors. EP 1265606; JP 2003506491; US 6630503; WO 0112186 .

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)	64984	4-amino-2-({[(phenylmethyl)oxy]carbonyl}amino)butanoic acid		C₁₂H₁₆N₂O₄	详情	详情
(II)	64985	methyl 4-amino-2-({[(phenylmethyl)oxy]carbonyl}amino)butanoate		C₁₃H₁₈N₂O₄	详情	详情
(III)	26295	(2S)-2-[(tert-butoxycarbonyl)(methyl)amino]-4-methylpentanoic acid	609-23-4	C₁₂H₂₃NO₄	详情	详情
(IV)	64986	methyl 4-({2-[{[(1,1-dimethylethyl)oxy]carbonyl}(methyl)amino]-4-methylpentanoyl}amino)-2-({[(phenylmethyl)oxy]carbonyl}amino)butanoate		C₂₅H₃₉N₃O₇	详情	详情
(V)	64987	methyl 2-amino-4-({2-[{[(1,1-dimethylethyl)oxy]carbonyl}(methyl)amino]-4-methylpentanoyl}amino)butanoate		C₁₇H₃₃N₃O₅	详情	详情
(VI)	64988	phenylmethyl 2-{[(2,5-dioxo-1-pyrrolidinyl)oxy]carbonyl}-1-pyrrolidinecarboxylate		C₁₇H₁₈N₂O₆	详情	详情
(VII)	64989	phenylmethyl 2-[9,12,12-trimethyl-3-[(methyloxy)carbonyl]-8-(2-methylpropyl)-7,10-dioxo-11-oxa-2,6,9-triazatridec-1-anoyl]-1-pyrrolidinecarboxylate		C₃₀H₄₆N₄O₈	详情	详情
(VIII)	64990	phenylmethyl 2-[({3-{[4-methyl-2-(methylamino)pentanoyl]amino}-1-[(methyloxy)carbonyl]propyl}amino)carbonyl]-1-pyrrolidinecarboxylate		C₂₅H₃₈N₄O₆	详情	详情

Extended Information