HCID 15284533, compound → HCID 22400442, compound

HRID 260744Notes

Reaction equation

HRID 260744 reaction equation
[CH2:1]([C:5]1[N:6]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2Cl)[C:7]([CH2:10][CH:11]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:12]([O:14][CH3:15])=[O:13])=[CH:8][N:9]=1)[CH2:2][CH2:3][CH3:4].[H][H]>CO.[Pt]=O>[CH2:1]([C:5]1[N:6]([CH2:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:7]([CH2:10][CH:11]([CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:12]([O:14][CH3:15])=[O:13])=[CH:8][N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 15284533HCID 15284533, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22400442HCID 22400442, compoundYield 18.1%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 887MethanolSolvent

Procedure

A solution of methyl 3-[2-n-butyl-{(2-chlorophenyl)methyl}-1H-imidazol-5-yl]-2-benzylpropanoate [Example 9] (0.75 g) in methanol (25 mL) was stirred with platinum oxide (0.07 g) at room temperature under one atmosphere of hydrogen for 18 hours. Column chromatographic separation of the crude product over silica gel with 10% methanol in ethyl acetate gave 0.52 g of the crude de-chlorinated product. This was further purified on a prep silica gel plate using 30% acetone in hexane to provide 0.125 g of methyl 3-[2-n-butyl-1-benzyl-1H-imidazol-5-yl]-2-benzylpropanoate as a syrup.

Workup

  1. customColumn chromatographic separation of the crude product over silica gel with 10% methanol in ethyl acetate
  2. customgave 0.52 g of the crude de-chlorinated product
  3. customThis was further purified on a prep silica gel plate

Sources & evidence

ORD record
ord-8b6330565e2a45dbadd3cd8ddae4c8f6
Source dataset
uspto-grants-1996_06
Patent number
US05530017

Reaction notes

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