N-t-butyloxycarbonyl-L-alanyl-L-prolyl-L-proline benzylester → N-t-butyloxycarbonyl-L-alanyl-L-prolyl-L-proline

HRID 2413731Notes

Reaction equation

HRID 2413731 reaction equation
C([O:8][C:9](=[O:34])[C@@H:10]1[CH2:14][CH2:13][CH2:12][N:11]1[C:15](=[O:33])[C@@H:16]1[CH2:20][CH2:19][CH2:18][N:17]1[C:21](=[O:32])[C@H:22]([CH3:31])[NH:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])C1C=CC=CC=1.[H][H]>CO.[C].[Pd]>[C:27]([O:26][C:24]([NH:23][C@H:22]([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:34])=[O:8])=[O:33])=[O:32])[CH3:31])=[O:25])([CH3:28])([CH3:29])[CH3:30]

Participants

5

Reactant 2

HCID 13389836N-t-butyloxycarbonyl-L-alanyl-L-prolyl-L-proline benzylesterHCID 178418361HCID 178418361, compound

Product 1

HCID 22827655N-t-butyloxycarbonyl-L-alanyl-L-prolyl-L-prolineYield 99.8%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

N-t-butyloxycarbonyl-L-alanyl-L-prolyl-L-proline benzylester (5.0 g, 10.6 m mole) was dissolved in methanol (100 ml) and hydrogen gas was passed through the solution in the presence of the palladium carbon as a catalyst for 3 hours. The catalyst was removed by filtration and the solvent was distilled off under reduced pressure. Thus obtained residue was dissolved in water and the solution was freeze-dried to give N-t-butyloxycarbonyl-L-alanyl-L-prolyl-L-proline (4.04 g).

Workup

  1. customThe catalyst was removed by filtration
  2. distillationthe solvent was distilled off under reduced pressure
  3. dissolutionThus obtained residue was dissolved in water
  4. customthe solution was freeze-dried

Sources & evidence

ORD record
ord-5f834158ad0144d7b17427348fa3791d
Source dataset
uspto-grants-1988_01
Patent number
US04719200

Reaction notes

Loading…