Benzyl chloroformate → (2S)-2-{[(benzyloxy)carbonyl]amino}-2-(3-hydroxyadamantan-1-yl)acetic acid

Participants

Reaction Steps

The (2S)-2-amino-2-(3-hydroxyadamantan-1-yl)acetic acid hydrochloride (20 g) was dissolved in 100 ml water at 25-30° C. The pH of the solution was adjusted to 8.5-9.5 with aqueous sodium hydroxide solution at 5° C. To the mixture benzyl chloroformate (10.7 g) was added and set aside for 4 h at 25-30° C. The reaction mass was washed with MTBE (25 ml) and the pH of the aqueous phase adjusted to 2-3 with dilute hydrochloric acid. Aqueous phase was extracted with ethyl acetate, the organic phase dried and evaporated to yield 26 g (95%) of the title product. M.P 55-58° C., H1NMR (300 MHz, CDCl3): 1.39-1.58 (m, 12H), 2.04-2.07 (s, 2H), 3.86-3.89 (dd, 1H), 4.98 (s, 2H), 5.11 (s, 1H), 7.0 (d, 1H), 7.16-7.27 (m, 5H).

Provenance & Evidence