N-Benzylaminocarbonyl-L-prolyl-L-proline benzyl ester → N-(Benzylaminocarbonyl)-L-prolyl-L-proline

HRID 1735394Notes

Reaction equation

HRID 1735394 reaction equation
C([O:8][C:9](=[O:32])[C@@H:10]1[CH2:14][CH2:13][CH2:12][N:11]1[C:15](=[O:31])[C@@H:16]1[CH2:20][CH2:19][CH2:18][N:17]1[C:21]([NH:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22])C1C=CC=CC=1>C1COCC1.[Pd]>[CH2:24]([NH:23][C:21]([N:17]1[CH2:18][CH2:19][CH2:20][C@H:16]1[C:15]([N:11]1[CH2:12][CH2:13][CH2:14][C@H:10]1[C:9]([OH:32])=[O:8])=[O:31])=[O:22])[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

4

Reactant 1

HCID 54203628N-Benzylaminocarbonyl-L-prolyl-L-proline benzyl ester

Product 1

HCID 53876803N-(Benzylaminocarbonyl)-L-prolyl-L-prolineYield 99.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Palladium-black (0.87 g) was added to a solution of N-(benzylaminocarbonyl)-L-prolyl-L-proline benzyl ester (43.55 g) in THF (400 ml), and the mixture was stirred at room temperature overnight under a hydrogen atmosphere. The reaction mixture was filtered and concentrated to give the title compound (34.5 g).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-4bd92b604c7e41169933f68401d3dfbc
Source dataset
uspto-grants-1996_07
Patent number
US05536737

Reaction notes

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