3-Benzyl 1-methyl 4-(4-(dibutylcarbamoyl)-1-phenethyl-1H-imidazol-2-yl)isophthalate → 2-(1-Benzyl-4-(dibutylcarbamoyl)-1H-imidazol-2-yl)-5-(methoxycarbonyl)benzoic acid

HRID 529015Notes

Reaction equation

HRID 529015 reaction equation
[CH2:1]([N:5]([CH2:41][CH2:42][CH2:43][CH3:44])[C:6]([C:8]1[N:9]=[C:10]([C:21]2[CH:30]=[CH:29][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:23][C:22]=2[C:31]([O:33]CC2C=CC=CC=2)=[O:32])[N:11]([CH2:13][CH2:14][C:15]2C=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:12]=1)=[O:7])[CH2:2][CH2:3][CH3:4]>CCOC(C)=O.[Pd]>[CH2:13]([N:11]1[CH:12]=[C:8]([C:6](=[O:7])[N:5]([CH2:41][CH2:42][CH2:43][CH3:44])[CH2:1][CH2:2][CH2:3][CH3:4])[N:9]=[C:10]1[C:21]1[CH:30]=[CH:29][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:23][C:22]=1[C:31]([OH:33])=[O:32])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 1

HCID 710610123-Benzyl 1-methyl 4-(4-(dibutylcarbamoyl)-1-phenethyl-1H-imidazol-2-yl)isophthalate

Product 1

HCID 710627152-(1-Benzyl-4-(dibutylcarbamoyl)-1H-imidazol-2-yl)-5-(methoxycarbonyl)benzoic acidYield 89.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-benzyl 1-methyl 4-(4-(dibutylcarbamoyl)-1-phenethyl-1H-imidazol-2-yl)isophthalate (100 mg, 0.17 mmol) in EtOAc (5 mL) was added Pd/C (10%). The reaction mixture was stirred under H2 atmosphere for 6 h, filtered through a small pad of CELITE® and washed thoroughly with MeOH. The solvents were removed in vacuo to provide the title compound (75 mg, 89%), which was used without further purification. MS(ESI+) m/z 506.2 (M+H)+.

Workup

  1. filtrationfiltered through a small pad of CELITE®
  2. washwashed thoroughly with MeOH
  3. customThe solvents were removed in vacuo

Sources & evidence

ORD record
ord-e59a8f1501944b408d89ede5aad28d90
Source dataset
uspto-grants-2016_05
Patent number
US09346795B2

Reaction notes

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