Triethylamine → HCID 90389340, compound

A rbf was charged with DL-serine methyl ester hydrochloride (1.49 g, 9.57 mmol, Sigma-Aldrich Chemical Company, Inc.), HATU (4.37 g, 11.49 mmol, Sigma-Aldrich Chemical Company, Inc.) and DCM (22 mL). 2-Fluoropropionic acid (0.75 ml, 9.57 mmol, Alfa Aesar, A Johnson Matthey Company) and triethylamine (3.3 ml, 23.93 mmol, Sigma-Aldrich Chemical Company, Inc.) were added and the reaction mixture was allowed to stir at rt overnight. The reaction mixture was diluted with water and extracted with DCM. The organic extract was washed with water, aqueous saturated NaHCO3 solution, brine, and dried over MgSO4. The solution was concentrated in vacuo and the crude product was purified by silica gel chromatography, eluting with a gradient of 1% to 10% MeOH in DCM, to provide methyl 2-(2-fluoropropanamido)-3-hydroxypropanoate (0.69 g, 3.60 mmol, 38% yield).

1. extractionextracted with DCM
2. extractionThe organic extract
3. washwas washed with water, aqueous saturated NaHCO3 solution, brine
4. dry with materialdried over MgSO4
5. concentrationThe solution was concentrated in vacuo
6. customthe crude product was purified by silica gel chromatography
7. washeluting with a gradient of 1% to 10% MeOH in DCM

ORD record

ord-19c7fe5164084959a9bc8c073c1aaf78

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09085576B2