HCID 66965934, compound → HCID 66966145, compound

HRID 1514868Notes

Reaction equation

HRID 1514868 reaction equation
C([O:3][C:4](=[O:34])[CH2:5][O:6][C:7]1[CH:12]=[C:11]([CH3:13])[C:10]([C:14]2[NH:18][C:17]3[CH:19]=[C:20]([C:23](=[O:32])[NH:24][C:25]4[CH:30]=[CH:29][CH:28]=[C:27]([Cl:31])[CH:26]=4)[CH:21]=[CH:22][C:16]=3[N:15]=2)=[C:9]([CH3:33])[CH:8]=1)C>[Li+].[OH-].C1COCC1>[Cl:31][C:27]1[CH:26]=[C:25]([NH:24][C:23]([C:20]2[CH:21]=[CH:22][C:16]3[N:15]=[C:14]([C:10]4[C:9]([CH3:33])=[CH:8][C:7]([O:6][CH2:5][C:4]([OH:34])=[O:3])=[CH:12][C:11]=4[CH3:13])[NH:18][C:17]=3[CH:19]=2)=[O:32])[CH:30]=[CH:29][CH:28]=1

Participants

4

Reactant 1

HCID 66965934HCID 66965934, compound

Product 1

HCID 66966145HCID 66966145, compound

Reagents, catalysts & solvents 2

HCID 3939Lithium HydroxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of {4-[6-(3-Chloro-phenylcarbamoyl)-1H-benzoimidazol-2-yl]-3,5-dimethyl-phenoxy}-acetic acid ethyl ester (71.7 mg) in 2N LiOH aqueous solution (1 mL) and THF (1 mL) was stirred at room temperature for 16 h. The mixture was washed with Et2O. The aqueous layer was acidified to pH 3 with 1N HCl aqueous solution, extracted with EtOAc, and the organic extracts were dried over Na2SO4, filtered and concentrated under reduced pressure to give {4-[6-(3-Chloro-phenylcarbamoyl)-1H-benzoimidazol-2-yl]-3,5-dimethyl-phenoxy}-acetic acid as white solid: MS (m/z) 444 (M+1); 1H NMR (MeOD, 400 MHz) δ 8.17 (s, 1H), 7.84 (d, 1H), 7.82 (s, 1H), 7.62 (d, 1H), 7.54 (d, 1H), 7.25 (t, 1H), 7.06 (dd, 1H), 6.70 (s, 2H), 4.59 (s, 2H), 2.06 (s, 6H).

Workup

  1. washThe mixture was washed with Et2O
  2. extractionextracted with EtOAc
  3. dry with materialthe organic extracts were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c78939828ad9456eb3fe9464af5b85ea
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

Loading…