Sodium hydride → N-Boc-O-(2-nitrophenyl)-D-serine

Participants

Reaction Steps

To a suspension of 1.84 g (0.0768M) of sodium hydride (NaH) in 50 mL of DMF at 0° C. under a nitrogen atmosphere was added dropwise a slurry of 7.39 g (0.0360M) of N-t-butoxycarbonyl-D-serine. After addition was complete, the reaction was warmed to room temperature and stirred for 45 minutes. The reaction was cooled to -5° C. and 4.04 mL (0.0384M) of 2-fluoronitrobenzene was added dropwise. The reaction was then warmed to room temperature and stirred for 1 hour. The reaction was quenched with an equal volume of water and extracted with ethyl acetate. The ethyl acetate extracts were reextracted with water (pH=9). The water layer was then adjusted to pH=7 and extracted with ethyl acetate. The water layer was then adjusted to pH=2 and extracted with ethyl acetate. The pH=2 ethyl acetate extracts were combined, dried, and evaporated to yield 8.98 g of product as an oil.

Provenance & Evidence