3-Cyanobenzoic acid → 3-(aminomethyl)benzoic acid
Reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([OH:8])=[O:7])#[N:2]>[Pd].CO>[NH2:2][CH2:1][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([OH:8])=[O:7]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
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.
Sources & evidence
- ORD record
- ord-8d463b849d6d4fd8922e072c5cb15182
- Source dataset
- uspto-grants-1995_02
- Patent number
- US05387671
Reaction notes
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