反応 #75416

反応方程式

L-proline

thiobenzoic acid

potassium carbonate

2-bromo-3-methoxybutyric acid chloride

→

1-[2-benzoylthio-3-methoxybutanoyl]-L-proline

溶媒

sodium hydroxide

sodium hydroxide

反応条件

後処理

1. 1
   抽出extracted with ethyl acetate
2. 2
   濃縮The organic layer is concentrated to dryness
3. 3
   その他the residue is chromatographed on a column of silica gel with benzene-acetic acid

実験手順

To a solution of L-proline (5.75 g.) in N sodium hydroxide (50 ml.) chilled in an ice bath, 2 N sodium hydroxide (25 ml.) and 2-bromo-3-methoxybutyric acid chloride [obtained from 2-bromo-3-methoxybutyric acid [J. Am. Chem. Soc., 71, 1096, (1949)] and thionyl chloride] (10.7 g.) are added, with vigorous stirring. After three hours, thiobenzoic acid (7.5 g.) and potassium carbonate (4.8 g.) are added and the mixture is stirred at room temperature overnight. The reaction mixture is acidified and extracted with ethyl acetate. The organic layer is concentrated to dryness and the residue is chromatographed on a column of silica gel with benzene-acetic acid to yield 1-[2-benzoylthio-3-methoxybutanoyl]-L-proline.

出典