benzyl O-[3(R)-acetoxy-2(S)-benzyloxycarbonylamino-1-oxobutyl]-N-trifluoroacetyl-L-serinate → O-[3(R)-acetoxy-2(S)-amino-1-oxobutyl]-N-trifluoroacetyl-L-serine
Reaction equation
[C:1]([O:4][C@H:5]([CH3:40])[C@H:6]([NH:29]C(OCC1C=CC=CC=1)=O)[C:7]([O:9][CH2:10][C@@H:11]([C:19]([O:21]CC1C=CC=CC=1)=[O:20])[NH:12][C:13](=[O:18])[C:14]([F:17])([F:16])[F:15])=[O:8])(=[O:3])[CH3:2]>[Pd].C(O)(=O)C>[C:1]([O:4][C@H:5]([CH3:40])[C@H:6]([NH2:29])[C:7]([O:9][CH2:10][C@@H:11]([C:19]([OH:21])=[O:20])[NH:12][C:13](=[O:18])[C:14]([F:16])([F:15])[F:17])=[O:8])(=[O:3])[CH3:2]Participants
4
Procedure
A mixture of benzyl O-[3(R)-acetoxy-2(S)-benzyloxycarbonylamino-1-oxobutyl]-N-trifluoroacetyl-L-serinate (1.42 g) and 10% palladium on activated carbon (300 mg) in acetic acid (50 ml) was hydrogenated under hydrogen at 40 psi at room temperature for 2 hours. The mixture was filtered with Celite (filter aid, trade mark, made by Nakarai Chemicals) and the filtrate was concentrated. The residue was diluted with water and lyophilized to give O-[3(R)-acetoxy-2(S)-amino-1-oxobutyl]-N-trifluoroacetyl-L-serine.