反应 #168130

反应方程式

methyl bromoacetate

dichloromethane

Et2Zn

[(S)-1-(4-chloro-phenyl)-ethyl]-(3-oxo-3-phenyl-propyl)-carbamic acid methyl ester

→

title compound

5-{[(S)-1-(4-Chloro-phenyl)-ethyl]-methoxycarbonyl-amino}-3-hydroxy-3-phenyl-pentanoic acid methyl ester

溶剂

1,2-dichloroethane

1,2-dichloroethane

反应条件

后处理

1. 1
   过滤the mixture was filtered through Celite which
2. 2
   萃取was extracted with an additional portion of dichloromethane
3. 3
   其他The organic phase was separated
4. 4
   洗涤washed with water
5. 5
   干燥dried (MgSO4)
6. 6
   其他The solvent was removed
7. 7
   其他the residue was purified by chromatography on silica gel (cyclohexane/ethyl acetate 85:15→70:30)

实验过程

Et2Zn (1 M in hexane, 55 mL) was added dropwise to [(S)-1-(4-chloro-phenyl)-ethyl]-(3-oxo-3-phenyl-propyl)-carbamic acid methyl ester (3.80 g) dissolved in 1,2-dichloroethane (30 mL) and chilled to 0° C. under argon atmosphere. Then, (Ph3P)3RhCl (0.50 g) was added followed by the dropwise addition of methyl bromoacetate (1.0 mL) dissolved in 1,2-dichloroethane (10 mL). The resulting solution was stirred at 0-5° C. for 1 h and at ambient temperature for another 1.5 h. The solution was poured into ice-cold half-saturated aqueous NH4Cl solution (150 mL). After addition of dichloromethane, the mixture was filtered through Celite which was extracted with an additional portion of dichloromethane. The organic phase was separated and washed with water and dried (MgSO4). The solvent was removed and the residue was purified by chromatography on silica gel (cyclohexane/ethyl acetate 85:15→70:30) to give the title compound as a mixture of two diastereomers.

来源