Cyclohexene → N-[3-carboxy-2-(2-methylpropyl)propenoyl]-O-methyl-L-tyrosine N-methylamide

Reaction equation

[CH3:1][NH:2][C:3](=[O:33])[C@H:4]([CH2:24][C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=1)[NH:5][C:6](=[O:23])[C:7]([CH2:19][CH:20]([CH3:22])[CH3:21])=[CH:8][C:9]([O:11]CC1C=CC=CC=1)=[O:10].C1CCCCC=1>C(O)C.[Pd]>[CH3:1][NH:2][C:3](=[O:33])[C@H:4]([CH2:24][C:25]1[CH:26]=[CH:27][C:28]([O:31][CH3:32])=[CH:29][CH:30]=1)[NH:5][C:6](=[O:23])[C:7]([CH2:19][CH:20]([CH3:21])[CH3:22])=[CH:8][C:9]([OH:11])=[O:10]

Participants

Procedure

E and Z N-[3-(benzyloxycarbonyl)-2-(2-methylpropyl)propenoyl]-O-methyl-L-tyrosine N-methylamide (3.0 g.) was heated under reflux for 2 hours in ethanol (60 mls.) and cyclohexene (30 mls.) in the presence of 10% palladium on charcoal (0.75 g.). The resultant reaction mixture was filtered through Celite and the solvent removed by evaporation in vacuo to yield a gum. This gum was crystallized from methanol/water to yield E and Z N-[3-carboxy-2-(2-methylpropyl)propenoyl]-O-methyl-L-tyrosine N-methylamide.