3-Cyanobenzoic acid → 3-(aminomethyl)benzoic acid

Participants

Reaction Steps

N-Boc-(3RS)-Aminomethylcyclohexanecarboxylic acid was prepared from commercially available 3-cyanobenzoic acid by catalytic hydrogenation using palladium on charcoal in methanol to give the 3-aminomethylbenzoic acid. This was reacted with Boc-ON, followed by hydrogenation with rhodium on aluminum oxide in methanol to yield N-Boc-(3RS)-aminomethylcyclohexane carboxylic acid. FAB+MS: (M+H)+ =258 This compound was then incorporated into the peptide using the methods described in Example 1 and isolated by the method described in Example 2. The diastereomers were separated by RP-HPLC.

Provenance & Evidence