benzyl (1S)-5-[[(benzyloxy)carbonyl]amino]-1-formylpentylcarbamate -Drug Synthesis Database

【结构式】

【分子编号】28283

【品名】benzyl (1S)-5-[[(benzyloxy)carbonyl]amino]-1-formylpentylcarbamate

【CA登记号】

【分子式】C₂₂H₂₆N₂O₅

【分子量】398.45892

【元素组成】C 66.32% H 6.58% N 7.03% O 20.08%

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：(III)

Treatment of N,N'-di-Cbz-lysine (I) with ethyl chloroformate and N-ethyl morpholine, followed by condensation of the resulting mixed anhydride with N,O-dimethylhydroxylamine provided the corresponding N-methoxyamide (II). This was reduced with LiAlH4 in cold Et2O to furnish aldehyde (III). The title compound was then obtained by reductive condensation of (III) with D-proline (IV) in the presence of NaBH3CN.

参考文献中间体

合成目标

【1】 Masini, I.; Fantetti, L.; Giotti, A.; Roncucci, G.; Adembri, G.; Synthesis and antinociceptive activity of some novel nonpeptide derivatives of interleukin-1beta (193-195) sequence. Arzneim-Forsch Drug Res 1999, 49, 2, 137.
【2】 Roncucci, G.; Giotti, A.; Adembri, G.; Fantetti, L.; Masini, I. (Molteni L. & C. SpA); Amines exhibiting analgesic action, their preparation and use. WO 9633210 .

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)	28281	(2S)-2,6-bis[[(benzyloxy)carbonyl]amino]hexanoic acid		C₂₂H₂₆N₂O₆	详情	详情
(II)	28282	benzyl (1S)-5-[[(benzyloxy)carbonyl]amino]-1-[[methoxy(methyl)amino]carbonyl]pentylcarbamate		C₂₄H₃₁N₃O₆	详情	详情
(III)	28283	benzyl (1S)-5-[[(benzyloxy)carbonyl]amino]-1-formylpentylcarbamate		C₂₂H₂₆N₂O₅	详情	详情
(IV)	28284	D-proline	344-25-2	C₅H₉NO₂	详情	详情

Extended Information