1-benzyl-5-oxoproline -Drug Synthesis Database

【结构式】

【分子编号】41961

【品名】1-benzyl-5-oxoproline

【CA登记号】

【分子式】C₁₂H₁₃NO₃

【分子量】219.24016

【元素组成】C 65.74% H 5.98% N 6.39% O 21.89%

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)

Coupling of N-benzylpyroglutamic acid (I) with 4-nitrophenylalanine methyl ester (II) by means of O-benzotriazolyl-N,N,N’,N’-tetramethyluronium hexafluorophosphate (HBTU) produced amide (III). After stannous chloride mediated reduction of the nitro group of (III), the resulting aniline (IV) was coupled with 2,6-dichlorobenzoic acid (V) to give diamide (VI). The title carboxylic acid was then obtained by ester hydrolysis with NaOH.

参考文献中间体

合成目标

【1】 Guthrie, R.W.; Chen, L.; Tilley, J.W.; et al.; N-Benzylpyroglutamyl-L-phenylanine derivatives as VCAM/VLA-4 antagonists. Bioorg Med Chem Lett 2000, 10, 8, 729.

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)	41961	1-benzyl-5-oxoproline		C₁₂H₁₃NO₃	详情	详情
(II)	15342	methyl (2S)-2-amino-3-(4-nitrophenyl)propanoate		C₁₀H₁₂N₂O₄	详情	详情
(III)	41962	methyl (2S)-2-[[(1-benzyl-5-oxo-2-pyrrolidinyl)carbonyl]amino]-3-(4-nitrophenyl)propanoate		C₂₂H₂₃N₃O₆	详情	详情
(IV)	41963	methyl (2S)-3-(4-aminophenyl)-2-[[(1-benzyl-5-oxo-2-pyrrolidinyl)carbonyl]amino]propanoate		C₂₂H₂₅N₃O₄	详情	详情
(V)	41964	2,6-dichlorobenzoic acid	50-30-6	C₇H₄Cl₂O₂	详情	详情
(VI)	41965	methyl (2S)-2-[[(1-benzyl-5-oxo-2-pyrrolidinyl)carbonyl]amino]-3-[4-[(2,6-dichlorobenzoyl)amino]phenyl]propanoate		C₂₉H₂₇Cl₂N₃O₅	详情	详情

Extended Information