N-(carbobenzyloxyaminosulfonyl)-2-propyl-DL-alanine methyl ester → N-aminosulfonyl-2-propyl-DL-alanine methyl ester
Reaction equation
[CH3:1][O:2][C:3](=[O:24])[C:4]([CH2:21][CH2:22][CH3:23])([CH3:20])[NH:5][S:6]([NH:9]C(OCC1C=CC=CC=1)=O)(=[O:8])=[O:7]>[Pd].CO>[CH3:1][O:2][C:3](=[O:24])[C:4]([CH2:21][CH2:22][CH3:23])([CH3:20])[NH:5][S:6]([NH2:9])(=[O:7])=[O:8]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
A mixture of N-(carbobenzyloxyaminosulfonyl)-2-propyl-DL-alanine methyl ester (22.35 g, 62.36 mmol), methanol (200 mL) and 10% palladium on Carbon (1.0 g) was placed on a Parr hydrogenator at 60 psi for 1.5 hours. The reaction mixture was passed through a pad of CELITE®, and the filtrate was concentrated in vacuo to afford 11.16 g (79.8%) of N-aminosulfonyl-2-propyl-DL-alanine methyl ester (Formula VII: R=CH3 ; R1 =propyl; R2 =CH3; R3 =H).