Sodium Bicarbonate → Methyl (2S,3S)-3-hydroxy-2-[(triphenylmethyl)amino]butanoate

Participants

Reaction Steps

A solution of the methyl O-benzoyl-N-trityl-L-allothreoninate (1.24 g, 2.59 mmol) dissolved in 15 mL of anhydrous methanol was treated with 0.1 mL of a 25% solution of sodium methoxide in methanol. The reaction mixture was stirred under N2 for 2 days. The reaction was then treated with 10 mL of saturated aqueous NaHCO3 solution and the methanol was removed under reduced pressure. The reaction mixture was then treated with 30 mL of ethyl acetate and washed successively with H2O and brine. The organic portion was dried over Na2SO4, filtered and concentrated under reduced pressure to give a colorless solid. Crystallization from ethyl acetate and hexanes gave methyl N-trityl-L-allothreoninate (0.60 g) as colorless crystals.

Provenance & Evidence