1-[(tert-Butoxycarbonyl)methyl]-Nalpha-benzyloxycarbonyl-D-tryptophan → 1-[(tert-Butoxycarbonyl)methyl]-D-tryptophan
Reaction equation
[C:1]([O:5][C:6]([CH2:8][N:9]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:11]([CH2:12][C@H:13]([C:25]([OH:27])=[O:26])[NH:14]C(OCC2C=CC=CC=2)=O)=[CH:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6]([CH2:8][N:9]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:11]([CH2:12][C@H:13]([C:25]([OH:27])=[O:26])[NH2:14])=[CH:10]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
The 136 g of product obtained in Step A are diluted with 1.5 liters of methanol and hydrogenated in the presence of 5 g of 10% Pd/C under an H2 pressure of 1.2 bars. After 12 hours of reaction at ambient temperature, the solution is filtered and then concentrated in vacuo. 87 g of the expected product are obtained in the form of a beige powder.