Réaction #75210

Équation de réaction

L-proline

thiobenzoic acid

potassium carbonate

2-bromo-3-methoxybutyric acid chloride

→

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

Solvants

sodium hydroxide

sodium hydroxide

Conditions de réaction

Traitement

1. 1
   Extractionextracted with ethyl acetate
2. 2
   ConcentrationThe organic layer is concentrated to dryness
3. 3
   Autrethe residue is chromatographed on a column of silica gel with benzene-acetic acid

Mode opératoire

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.

Source