1-Amino-2-propanol → Ethyl 2-(2-hydroxypropylamino)-2-oxo-acetate

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)+.

1. extractionextracted with DCM (2×100 mL)
2. washwashed with water (2×50 mL) and brine (50 mL)
3. dry with materialdried over Na2SO4
4. customevaporated to dryness
5. customThe crude product is purified by silica gel chromatography
6. washeluting with hexane:ethyl acetate (3.0:7.0)

ORD record

ord-450d4c0fee3549558dbf0a9a1323f99c

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08822486B2