Methanol → 2-(Aminosulfonylamino)pentanoic acid methyl ester
Reaction equation
C([NH:11][S:12]([NH:15][CH:16]([CH2:20][CH2:21][CH3:22])[C:17]([OH:19])=[O:18])(=[O:14])=[O:13])(OCC1C=CC=CC=1)=O.[CH3:23]O>[Pd]>[CH3:23][O:19][C:17](=[O:18])[CH:16]([NH:15][S:12]([NH2:11])(=[O:14])=[O:13])[CH2:20][CH2:21][CH3:22]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 2-(N-carbobenzyloxyaminosulfonyl)aminopentanoic acid (46.7 g), methanol (350 mL) and 10% palladium on carbon (3.0 g) was hydrogenated at 55 psi for about 2 hours. The catalyst was removed by filtration through CELITE®, the solvent was removed in vacuo and the residue was purified by column chromatography on silica eluting with 50% ethyl acetate/hexane to afford 25.6 g (90%) of 2-(aminosulfonylamino)pentanoic acid methyl ester (Formula V: R=CH3 ; R1 =propyl; R2 =H; R3 =H), m.p. 63°-64° C.