Réaction #156269

Équation de réaction

Chloro-oxo-acetic acid ethyl ester

1-amino-propan-2-ol

triethylamine

→

title compound

Rendement 31.0%

Ethyl 2-(2-hydroxypropylamino)-2-oxo-acetate

Rendement 31.0%

Solvants

water

DCM

Conditions de réaction

Traitement

1. 1
   Extractionextracted with DCM (2×100 mL)
2. 2
   Lavagewashed with water (2×50 mL) and brine (50 mL)
3. 3
   Séchagedried over Na2SO4
4. 4
   Autreevaporated to dryness
5. 5
   AutreThe crude product is purified by silica gel chromatography
6. 6
   Lavageeluting with hexane:ethyl acetate (3.0:7.0)

Mode opératoire

To a stirred solution of 1-amino-propan-2-ol (15.0 g, 199.7 mmol) in DCM (150.0 mL), is added triethylamine (43.30 mL, 299.56 mmol) at 0° C. Chloro-oxo-acetic acid ethyl ester (22.35 mL, 199.7 mmol) is added dropwise to the reaction mixture at 0° C. and the reaction mixture is stirred for 16 hours at room temperature. The mixture is diluted with water (100 mL) at 0° C., extracted with DCM (2×100 mL), washed with water (2×50 mL) and brine (50 mL), dried over Na2SO4, and evaporated to dryness. The crude product is purified by silica gel chromatography, eluting with hexane:ethyl acetate (3.0:7.0) to give the title compound as a pale yellow gel (10.7 g, 31.0%). ESI/MS m/z 176.2 (M+H)+.

Source