N-(tert-butoxycarbonyl)-O-(3-nitrobiphenyl-2-yl)-L-serine → O-(3-aminobiphenyl-2-yl)-N-(tert-butoxycarbonyl)-L-serine
Reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:27]([OH:29])=[O:28])[CH2:10][O:11][C:12]1[C:17]([N+:18]([O-])=O)=[CH:16][CH:15]=[CH:14][C:13]=1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>[Pd].CCO>[NH2:18][C:17]1[C:12]([O:11][CH2:10][C@@H:9]([C:27]([OH:29])=[O:28])[NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])=[C:13]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:14]=[CH:15][CH:16]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
In an autoclave containing 500 mg of 35 (1.243 mmol), 54 mg of Pd/C (10%) and 33 mL of EtOH, hydrogenation is performed at 2 bar for 10 h at 20° C. After filtration of the catalyst on celite, the solvent is evaporated and 284 mg of expected product 36 are obtained, which product is used directly for the next step.