Sulfuric Acid → (2S,3S)-benzyl 3-azido-2-(tert-butoxycarbonylamino)butanoate

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-benzyl 3-tert-butyl(4S,5R)-5-methyl-1,2,3-oxathiazolidine-3,4-dicarboxylate 2,2-dioxide (17.13 g, 46.1 mmol) in DMF (171 ml) at −40° C. was added sodium azide (3.9 g, 60.0 mmol) in portions, and the mixture was stirred at −40° C. then slowly warmed to rt over 4 h. Added 20% aq. NaCl (100 ml), followed by dropwise addition of 2 N H2SO4 (10 ml). The reaction was stirred at rt for 3 h, then partitioned between H2O and EtOAc, and the aqueous layer was extracted with EtOAc. The combined organic layers were washed with H2O and brine, dried over Na2SO4, filtered, and concentrated to afford (2S,3S)-benzyl 3-azido-2-(tert-butoxycarbonylamino)butanoate as a slightly yellowish glue (14.8 g, 96%).

Provenance & Evidence