HCID 86723607, compound → HCID 86723608, compound
Reaction equation
[CH3:1][O:2][C:3]([NH:5][C@@H:6]([C@@H:27]([CH3:30])[CH2:28][CH3:29])[C:7]([N:9]1[C@H:13]([C:14]([O:16]CC2C=CC=CC=2)=[O:15])[CH2:12][C@@H:11]2[CH2:24][CH2:25][CH2:26][C@H:10]12)=[O:8])=[O:4]>[Pd].C(O)C>[CH3:1][O:2][C:3]([NH:5][C@@H:6]([C@@H:27]([CH3:30])[CH2:28][CH3:29])[C:7]([N:9]1[C@H:13]([C:14]([OH:16])=[O:15])[CH2:12][C@@H:11]2[CH2:24][CH2:25][CH2:26][C@H:10]12)=[O:8])=[O:4]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
To a 250 mL round bottom flask charged with a stirbar and (2S,3aS,6aS)-benzyl 1-((2S,3S)-2-(methoxycarbonylamino)-3-methylpentanoyl)octahydrocyclopenta[b]pyrrole-2-carboxylate (19.53 g crude, assumed 35.49 mmol) was added 10% Palladium on carbon (3.55 g). Ethanol was poured over the mixture and the reaction mixture was evacuated and flushed with hydrogen gas three times. The suspension was stirred at room temperature under and atmosphere of hydrogen for 3 days. Upon completion, the reaction mixture was filtered through celite and concentrated to give (2S,3aS,6aS)-1-((2S,3S)-2-(methoxycarbonylamino)-3-methylpentanoyl)octahydrocyclopenta[b]pyrrole-2-carboxylic acid (13.65 g, >99%). LCMS-ESI+ calc'd for C16H26N2O5: 327.18. Found: 327.13.