Methanol → HCID 66697243, compound

HRID 2386793Notes

Reaction equation

HRID 2386793 reaction equation
C[O:2][C:3](=[O:39])[C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[CH:16]=[CH:15][C:14]([CH:17]([CH3:36])[C:18]([C:24]3[CH:35]=[CH:34][C:27]4[N:28]([CH3:33])[C:29](=[O:32])[N:30]([CH3:31])[C:26]=4[CH:25]=3)([OH:23])[C:19]([F:22])([F:21])[F:20])=[C:13]([Cl:37])[CH:12]=2)=[CH:6][C:5]=1[F:38].[Li+].[OH-].CO>C1COCC1>[Cl:37][C:13]1[CH:12]=[C:11]([CH:16]=[CH:15][C:14]=1[CH:17]([CH3:36])[C:18]([C:24]1[CH:35]=[CH:34][C:27]2[N:28]([CH3:33])[C:29](=[O:32])[N:30]([CH3:31])[C:26]=2[CH:25]=1)([OH:23])[C:19]([F:21])([F:22])[F:20])[O:10][C:7]1[CH:8]=[CH:9][C:4]([C:3]([OH:39])=[O:2])=[C:5]([F:38])[CH:6]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 66697274HCID 66697274, compound

Product 1

HCID 66697243HCID 66697243, compoundYield 76.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 4-{3-chloro-4-[2-(1,3-dimethyl-2-oxo-2,3-dihydro-1H-benzoimidazol-5-yl)-3,3,3-trifluoro-2-hydroxy-1-methyl-propyl]-phenoxy}-2-fluoro-benzoic acid methyl ester (400 mg) aqueous 1N LiOH (1.5 ml), MeOH (5 ml) and THF (10 ml) were added. The resulting solution was stirred for 1 h at room temperature. Volatile solvents were removed in vacuo. The residual aqueous solution was diluted with water (10 ml) and then acidified to pH 6 with 1 N aqueous HCl and extracted with EtOAc. The combined EtOAc layers were dried over Na2SO4 and concentrated to give the title compound (300 mg) as a white foam. MS (m/e)=551.2 [M+H+].

Workup

  1. customVolatile solvents were removed in vacuo
  2. additionThe residual aqueous solution was diluted with water (10 ml)
  3. extractionextracted with EtOAc
  4. dry with materialThe combined EtOAc layers were dried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2f467bd55faa453f8c5e2ad321f0b39d
Source dataset
uspto-grants-2012_09
Patent number
US08268820B2

Reaction notes

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