Benzyl chloroformate → Boc-dap(Z)-OH

Participants

Reaction Steps

To a mixture of 3-amino-N-(tert-butoxycarbonyl)alanine (5.0 g, 25 mmol), potassium hydroxide (1.6 g, 29 mmol) and potassium carbonate (6.9 g, 29 mmol) in THF (60 mL) and water (20 mL) was added dropwise benzyl chloroformate (5.0 g, 29 mmol) at 0° C. The reaction mixture was allowed to warm to ambient temperature. After 16 hours, the reaction mixture was concentrated under reduced pressure, and the residue was washed with water followed by petroleum ether to afford 3-{[(benzyloxy)carbonyl]amino}-N-(tert-butoxycarbonyl)alanine. MS ESI calc'd. for C16H23N2O6 [M+H]+ 339. found 339. 1H NMR (300 MHz, CD3OD) δ 7.33-7.26 (m, 5H), 5.03 (s, 2H), 4.03-4.01 (m, 1H), 3.49-3.35 (m, 2H), 1.44 (s, 9H).

Provenance & Evidence