Methanol → N-[1-(5-Bromo-2-fluoro-phenyl)-2-hydroxy-1-hydroxymethyl-ethyl]-2-chloro-acetamide

A solution of chloro-acetyl chloride (6.39 ml, 80 mmol) in 10 ml ACN was added dropwise to a mixture of 2-amino-2-(5-bromo-2-fluoro-phenyl)-propane-1,3-diol (5.3 g, 20 mmol) and K2CO3 (11.1 g, 80 mmol) in 90 ml ACN while the temperature did not rise above 35° C. The mixture was stirred for 2 h. MeOH (40 ml, 99 mmol) were added and after 5 min stirring the mixture was filtered over celite and washed with MeOH. The filtrate was acidified with citric acid solution (10%, aqueous) (pH 4-5) and partly evaporated. The remaining aqueous layer was extracted with EtOAc. The organic layer was washed with NaHCO3 solution (10%, aqueous) and brine, dried with Na2SO4 and evaporated to provide the title compound as an off-white solid.

1. customdid not rise above 35° C
2. stirringstirring the mixture
3. filtrationwas filtered over celite
4. washwashed with MeOH
5. custompartly evaporated
6. extractionThe remaining aqueous layer was extracted with EtOAc
7. washThe organic layer was washed with NaHCO3 solution (10%, aqueous) and brine
8. dry with materialdried with Na2SO4
9. customevaporated

ORD record

ord-17c5b9604e7b41558bd1acd3b51cf8b8

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08846658B2