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

HRID 529010Notes

Reaction equation

HRID 529010 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]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:12]=1)=[O:7])[CH2:2][CH2:3][CH3:4]>CO.[Pd]>[CH2:41]([N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[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]([OH:33])=[O:32])[N:11]([CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:12]=1)=[O:7])[CH2:42][CH2:43][CH3:44]

Participants

4

Reactant 1

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

Product 1

HCID 710622442-(4-(Dibutylcarbamoyl)-1-phenethyl-1H-imidazol-2-yl)-5-(methoxycarbonyl)benzoic acidYield 93.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 3-benzyl 1-methyl 4-(4-(dibutylcarbamoyl)-1-phenethyl-1H-imidazol-2-yl)isophthalate (170 mg, 0.28 mmol) in MeOH (5.0 mL) was added Pd/C (10%). The reaction mixture was stirred under H2 atmosphere for 2 h. The reaction mixture was then filtered through a small pad of CELITE®, washing thoroughly with MeOH. The filtrate was concentrated in vacuo to provide the title compound (133 mg, 92%), which was used without further purification. MS(ESI+) m/z 506.2 (M+H)+.

Workup

  1. filtrationThe reaction mixture was then filtered through a small pad of CELITE®
  2. washwashing thoroughly with MeOH
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-5620c9db71e748578d629943587dc1f9
Source dataset
uspto-grants-2016_05
Patent number
US09346795B2

Reaction notes

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