Water → 256461-28-6

HRID 278486Notes

Reaction equation

HRID 278486 reaction equation
[BH4-].[Na+].[C:3]([C:6]1[N:7]=[CH:8][N:9]([CH:11]([CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:12](OCC)=[O:13])[CH:10]=1)(=[O:5])[NH2:4].O>CO>[OH:13][CH2:12][CH:11]([N:9]1[CH:10]=[C:6]([C:3]([NH2:4])=[O:5])[N:7]=[CH:8]1)[CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 22628493HCID 22628493, compound

Product 1

HCID 3009363256461-28-6Yield 103.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

NaBH4 (491 mg) was added portionwise to an ice cooled solution of ethyl 2-(4-carbamoyl-1-imidazolyl)-4-phenylbutyrate (obtained in Preparation 2) (391 mg) in methanol (20 ml) under an nitrogen atmosphere. After the addition was completed, the reaction mixture was stirred at room temperature for 30 minutes. Water was added, and the resulting mixture was stirred for several minutes and then evaporated under reduced pressure. The residue was partitioned between chloroform and water. The organic layer was washed with brine and dried over sodium sulfate. Evaporation of the solvent under reduced pressure gave 1-(1-hydroxy-4-phenyl-2-butyl)imidazole-4-carboxamide (347 mg) as a white solid.

Workup

  1. additionAfter the addition
  2. stirringthe resulting mixture was stirred for several minutes
  3. customevaporated under reduced pressure
  4. customThe residue was partitioned between chloroform and water
  5. washThe organic layer was washed with brine
  6. dry with materialdried over sodium sulfate
  7. customEvaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-1f8f8e76e5e54b13a1e25a3dc6c2fd86
Source dataset
uspto-grants-2002_03
Patent number
US06359145B1

Reaction notes

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