Methanol → 2-(N-carbobenzyloxyaminosulfonyl)aminopentanoic acid methyl ester

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Reaction Steps

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 XIV: R=CH3 ; R1 =H; R2 =propyl; R3 =H), m.p. 63°-64° C.

Provenance & Evidence