Benzyl chloroformate → ((Benzyloxy)carbonyl)-L-allothreonine

Participants

Reaction Steps

Benzylchloroformate (0.35 ml; 2.3 mmol) was added to a mixture of L-allothreonine (0.25 g; 2.1 mmol) and NaHCO3 (435 mg; 5.18 mmol) in 2.5 ml of H2O at RT. After 3 h, the reaction mixture was partitioned between Et2O and H2O. The aqueous layer was washed with Et20, acidified to pH <2 with 6N HCl, and extracted with CH2Cl2. The organic layer was dried (MgSO4) and concentrated to afford 320 mg (63%) of Cbz-L-allothreonine.

Provenance & Evidence