HCID 15228255, compound → HCID 57240357, compound

HRID 1033855Notes

Reaction equation

HRID 1033855 reaction equation
C([O:8][C:9]([C:11]1[N:12]=[CH:13][O:14][C:15]=1[CH2:16][CH2:17][NH:18][C:19](=[O:48])[C@H:20]([CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[NH:21][C@H:22]([C:31]([O:33]CC1C=CC=CC=1)=[O:32])[CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:10])C1C=CC=CC=1>CN(C)C=O.[Pd]>[C:9]([C:11]1[N:12]=[CH:13][O:14][C:15]=1[CH2:16][CH2:17][NH:18][C:19](=[O:48])[C@H:20]([CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[NH:21][C@H:22]([C:31]([OH:33])=[O:32])[CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([OH:10])=[O:8]

Participants

4

Reactant 1

HCID 15228255HCID 15228255, compound

Product 1

HCID 57240357HCID 57240357, compoundYield 84.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

1.8 g of 4-benzyloxycarbonyl-5-{2-[N-((1S)-1-benzyloxycarbonyl-3-phenylpropyl)-(L)-phenylalanyl]aminoethyl}oxazole was subjected to catalytic hydrogenolysis in 50 ml of dimethylformamide in the presence of 100 mg of palladium-black at 3 atmospheric pressure for 5 hours. After removal of the catalyst by filtration, the solvent was removed. The crystals obtained were recrystallized from methanol to obtain 1.1 g of 4-carboxy-5-{2-[N-((1S)-1-carboxy-3-phenylpropyl)-(L)-phenylalanyl]aminoethyl}oxazole.

Workup

  1. customAfter removal of the catalyst
  2. filtrationby filtration
  3. customthe solvent was removed
  4. customThe crystals obtained
  5. customwere recrystallized from methanol

Sources & evidence

ORD record
ord-4bea9739927f4e52ae4a4e47a2df1e4a
Source dataset
uspto-grants-1994_05
Patent number
US05312826

Reaction notes

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