Hydrochloric Acid → HCID 178525951, compound

HRID 1433211Notes

Reaction equation

HRID 1433211 reaction equation
C[O:2][C:3](=[O:33])[CH:4]([OH:32])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[CH:31]=[CH:30][C:14]2[NH:15][C:16]([CH2:18][O:19][C:20]3[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=3)=[N:17][C:13]=2[CH:12]=1.CO.[OH-].[Li+].Cl>CCOC(C)=O.O>[OH:32][CH:4]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[CH:31]=[CH:30][C:14]2[NH:15][C:16]([CH2:18][O:19][C:20]3[CH:25]=[CH:24][C:23]([C:26]([F:28])([F:29])[F:27])=[CH:22][CH:21]=3)=[N:17][C:13]=2[CH:12]=1)[C:3]([OH:33])=[O:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 3939Lithium HydroxideHCID 178501756hydroxy-{2-[2-(4-trifluoromethyl-phenoxymethyl)-1H-benzoimidazol-5-yl]-phenyl}-acetic acid methyl ester

Product 1

HCID 178525951HCID 178525951, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of hydroxy-{2-[2-(4-trifluoromethyl-phenoxymethyl)-1H-benzoimidazol-5-yl]-phenyl}-acetic acid methyl ester (0.312 g, 0.684 mmol) in mixed solvent (14 mL, MeOH: H2O=3:1) at rt was added lithium hydroxide (LiOH) (0.098 g, 4.10 mmol). After stirring for 12 hours, the reaction mixture was diluted with EtOAc and acidified with aqueous 3N HCl. The organic layer was washed with brine, dried over Na2SO4, filtered, and the filtrate was concentrated under reduced pressure to afford the title compound as a white solid (0.296 g, 98%).

Workup

  1. washThe organic layer was washed with brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-12f74237b50847df8bf19b828761819c
Source dataset
uspto-grants-2009_11
Patent number
US07612211B2

Reaction notes

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