tert-Butyl (2S)-(adamant-1-ylmethoxycarbonylamino)-3-tert-butoxycarbonylaminopropionate → tert-Butyl (2S)-(adamant-1-ylmethoxycarbonylamino)-3-aminopropionate

Participants

Reaction Steps

A solution of 8.7 g (19.22 mmol) of tert-butyl (S)-2-(1-adamantylmethyloxycarbonylamino)-3-tert-butoxycarbonylamino-propionate in 180 ml of trifluoroacetic acid/dichloromethane (1:1) was added after 1 min to 1.5 l of ice-cold NaHCO3 solution, the mixture was extracted three times with dichloromethane and the dichloromethane phases were then dried over sodium sulfate. After filtration and removal of the solvent in vacuo, 6.35 g (94%) of tert-butyl (S)-3-amino-2-(1-adamantylmethyloxycarbonylamino)-propionate were obtained as a colorless solid.

Provenance & Evidence