Acetonitrile → HCID 13233120, compound

Temperature

-10 °C

3-Amino-1,2-propanediol (16.8 g, 184 mmol) was dissolved in MeOH (90 mL) at RT and the solution was diluted with ACN (acetonitrile) (550 mL) TEA (30.5 mL, 219 mmol) was added and the reaction mixture was cooled to −10° C. Chloroacetyl chloride (22.2 g, 15.6 mL, 197 mmol) was added dropwise at −10° C. for 2 h under nitrogen atmosphere and further maintained at −10° C. for 1 h and the reaction mixture was allowed to RT and stirred overnight (15 h). The solvents were removed under vacuo. The residue was purified by flash column chromatography (normal phase, gradient 1 percent to 20 percent MeOH in EtOAc) to afford the title compound (20 g) as a colorless oil m/z 168.

1. additionwas added
2. temperaturefurther maintained at −10° C. for 1 h
3. customwas allowed to RT
4. customThe solvents were removed under vacuo
5. customThe residue was purified by flash column chromatography (normal phase, gradient 1 percent to 20 percent MeOH in EtOAc)

ORD record

ord-e1d43fadf6f24289bfdbb89a07dcc3b2

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09382216B2