Water → HCID 54454034, compound

HRID 741707Notes

Reaction equation

HRID 741707 reaction equation
[CH3:1][O:2][C:3](=[O:27])[C@H:4]([CH2:16][N:17]1[CH:21]=[CH:20][N:19]=[C:18]1[N:22]=[CH:23][N:24]([CH3:26])[CH3:25])[NH:5]C(OCC1C=CC=CC=1)=O.O>CO.[Pd]>[CH3:1][O:2][C:3](=[O:27])[C@H:4]([CH2:16][N:17]1[CH:21]=[CH:20][N:19]=[C:18]1[N:22]=[CH:23][N:24]([CH3:26])[CH3:25])[NH2:5]

Participants

5

Reactant 2

HCID 962WaterHCID 53723238HCID 53723238, compound

Product 1

HCID 54454034HCID 54454034, compoundYield 80.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

3- (2-Dimethylaminomethyleneaminoimidazol-1-yl)-N-(benzyloxycarbonyl)-L-alanine methyl ester (937 mg) was dissolved in methanol (25 ml), and 50% water-containing 10% Pd/C (468 mg) was added. Then, the mixture was vigorously stirred for 2 hours under an atmosphere of hydrogen. The catalyst was filtered off. The solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel flush column chromatography (eluent: 7% ammonia-containing ethanol-chloroform a 3:97) to give the title compound (482 mg).

Workup

  1. additionwas added
  2. filtrationThe catalyst was filtered off
  3. customThe solvent was evaporated under reduced pressure
  4. customThe resulting residue was purified by silica gel
  5. customflush column chromatography (eluent
  6. addition7% ammonia-containing ethanol-chloroform a 3:97)

Sources & evidence

ORD record
ord-b0619a4533104f7f8105864f2bf43589
Source dataset
uspto-grants-1996_09
Patent number
US05552427

Reaction notes

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