Lithium Hydroxide → {4-[6-(4-tert-Butylphenylcarbamoyl)-1H-benzoimidazol-2-yl]-3,5-dimethylphenoxy}-acetic acid

HRID 1515038Notes

Reaction equation

HRID 1515038 reaction equation
C[O:2][C:3](=[O:36])[CH2:4][O:5][C:6]1[CH:11]=[C:10]([CH3:12])[C:9]([C:13]2[NH:17][C:16]3[CH:18]=[C:19]([C:22](=[O:34])[NH:23][C:24]4[CH:29]=[CH:28][C:27]([C:30]([CH3:33])([CH3:32])[CH3:31])=[CH:26][CH:25]=4)[CH:20]=[CH:21][C:15]=3[N:14]=2)=[C:8]([CH3:35])[CH:7]=1.[Li+].[OH-]>O1CCCC1>[C:30]([C:27]1[CH:28]=[CH:29][C:24]([NH:23][C:22]([C:19]2[CH:20]=[CH:21][C:15]3[N:14]=[C:13]([C:9]4[C:8]([CH3:35])=[CH:7][C:6]([O:5][CH2:4][C:3]([OH:36])=[O:2])=[CH:11][C:10]=4[CH3:12])[NH:17][C:16]=3[CH:18]=2)=[O:34])=[CH:25][CH:26]=1)([CH3:33])([CH3:32])[CH3:31]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 66965814{4-[6-(4-tert-butylphenylcarbamoyl)-1H-benzoimidazol-2-yl]-3,5-dimethylphenoxy}-acetic acid methyl ester

Product 1

HCID 66966192{4-[6-(4-tert-Butylphenylcarbamoyl)-1H-benzoimidazol-2-yl]-3,5-dimethylphenoxy}-acetic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of {4-[6-(4-tert-butylphenylcarbamoyl)-1H-benzoimidazol-2-yl]-3,5-dimethylphenoxy}-acetic acid methyl ester (0.1727 g, 0.356 mmol) in tetrahydrofuran (5 mL) was added LiOH (1 mL of a 4M solution) and the mixture was stirred at ambient temperature for 18 h. The solvent was removed under reduced pressure and the residue was taken up in water, brought to pH 4 and the solid filtered to the title compound. 1H-NMR (DMSO-d6, 400 MHz): δ 12.97 (s, broad, 1H), 12.72 (d, J=24.76 Hz, 1H), 10.11 (d, J=15.16 Hz, 1H), 10.11 (d, J=15.16 Hz, 1H), 8.31 (s, 0.5H), 8.06 (s, 0.5H), 7.75-7.81 (m, 1H), 7.63-7.71 (m, 2.5H), 7.51 (d, J=8.34 Hz, 0.5H,) 7.30 (d, J=8.59 Hz, 2H), 6.71 (s, 2H), 4.68 (s, 2H), 2.03 (s, 6H), 1.22 (s, 9H). MS (m/z) 472.2 (M+1).

Workup

  1. customThe solvent was removed under reduced pressure
  2. filtrationthe solid filtered to the title compound

Sources & evidence

ORD record
ord-b140315491e445d88a2f93ceafc4c00e
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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