Z-Dap-OH → (S)-tert-Butyl 3-amino-2-(((benzyloxy)carbonyl)amino)propanoate

Participants

Reaction Steps

2.5 ml of concentrated HClO4 is added without exceeding 5° C. to a suspension of 5 g of N-alpha-[(phenylmethoxy)carbonyl]-L-alpha,beta-diaminopropionic acid 10-1 (alternative nomenclature: (3-amino-N-[(phenylmethoxy)carbonyl]-L-alanine) in 25 ml of tertbutyl acetate cooled down to 0° C., the temperature of the reaction medium is allowed to rise to 20° C. and agitation is carried out for 4 days at 20° C. The reaction medium is poured into a sodium bicarbonate/ice solution (300 ml/200 ml), followed by extracting with ethyl acetate, filtering, decanting, drying the organic phase, evaporating under reduced pressure until a dry extract is obtained corresponding to the expected product (3.2 g) which is used as it is in the following reaction.

Provenance & Evidence