(Z)-2-(2-oxo-1-pyrrolidinyl)-2-butenoyl chloride -Drug Synthesis Database

【结构式】

【分子编号】61960

【品名】(Z)-2-(2-oxo-1-pyrrolidinyl)-2-butenoyl chloride

【CA登记号】

【分子式】C₈H₁₀ClNO₂

【分子量】187.62564

【元素组成】C 51.21% H 5.37% Cl 18.9% N 7.47% O 17.05%

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)

The condensation of 2-pyrrolidone (I) with 2-oxobutyric acid (II) in refluxing toluene gives 2-(2-oxopyrrolidin-1-yl)-2-butenoic acid (III), which is treated with PCl5 in THF to yield the acyl chloride (IV). The reaction of (IV) with dry ammonia affords the corresponding amide (V), which is finally submitted to an asymmetric hydrogenation with H2 over a chiral Rh catalyst to provide the desired chiral butyramide.

参考文献中间体

合成目标

【1】 Michel, P.; Differding, E.; Pasau, P.; Kenda, B.; Lallemand, B.; Matagne, A.; Talaga, P. (UCB SA); 2-Oxo-1-pyrrolidine derivs., processes for preparing them and their uses. WO 0162726; WO 0164637 .

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)	27397	2-Pyrrolidinone	616-45-5	C₄H₇NO	详情	详情
(II)	48297	2-oxobutyric acid	600-18-0	C₄H₆O₃	详情	详情
(III)	61959	(Z)-2-(2-oxo-1-pyrrolidinyl)-2-butenoic acid		C₈H₁₁NO₃	详情	详情
(IV)	61960	(Z)-2-(2-oxo-1-pyrrolidinyl)-2-butenoyl chloride		C₈H₁₀ClNO₂	详情	详情
(V)	61961	(Z)-2-(2-oxo-1-pyrrolidinyl)-2-butenamide		C₈H₁₂N₂O₂	详情	详情

Extended Information