Benzyl chloroformate → N-Z-D-serine methyl ester

To a solution of D-serine (10.5 g) in methanol (100 mL) was added thionyl chloride (8.76 mL) under ice-cooling. The reaction mixture was stirred at room temperature for 4 hr, and to the reaction mixture were added sodium hydrogen carbonate (25.2 g) and benzyl chloroformate (17.1 mL). The reaction mixture was stirred at room temperature overnight, the reaction mixture was added to water, and the mixture was extracted with ethyl acetate. The organic layer was separated, washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (10.3 g).

1. temperaturecooling
2. stirringThe reaction mixture was stirred at room temperature overnight
3. extractionthe mixture was extracted with ethyl acetate
4. customThe organic layer was separated
5. washwashed with saturated brine
6. dry with materialdried over magnesium sulfate
7. concentrationconcentrated under reduced pressure
8. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

ORD record

ord-867e1aa7a08b4944bf68d09f49d163f9

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08772277B2