Methanol → [[3'-Fluoro-4'-[(1-methylethyl)sulfonyl]-5-(trifluoromethyl)[1,1'-biphenyl]-2-yl]oxy]acetic acid

HRID 1695126Notes

Reaction equation

HRID 1695126 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:14]2[CH:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:17]=[CH:16][C:15]=2[O:24][CH2:25][C:26]([O:28]C)=[O:27])[CH:5]=[CH:6][C:7]=1[S:8]([CH:11]([CH3:13])[CH3:12])(=[O:10])=[O:9].CO>[OH-].[Na+]>[F:1][C:2]1[CH:3]=[C:4]([C:14]2[CH:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:17]=[CH:16][C:15]=2[O:24][CH2:25][C:26]([OH:28])=[O:27])[CH:5]=[CH:6][C:7]=1[S:8]([CH:11]([CH3:13])[CH3:12])(=[O:10])=[O:9]

Participants

4

Reactant 2

HCID 887MethanolHCID 91026486Methyl [[3'-fluoro-4'-[(1-methylethyl)sulfonyl]-5-(trifluoromethyl)[1,1'-biphenyl]-2-yl]oxy]acetate

Product 1

HCID 11704460[[3'-Fluoro-4'-[(1-methylethyl)sulfonyl]-5-(trifluoromethyl)[1,1'-biphenyl]-2-yl]oxy]acetic acid

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A solution of the product from step e) (140 mg) in NaOH (0.35 ml, 1 M), THY (2 ml) and MeOH (1 ml) was stirred for 2 h. The solvent was removed in vacuo and the residue was washed with ether, acidified (2M HCl) and extracted with DCM (thrice). The organic extracts were dried (MgSO4), evaporated and crystallised from isohexane—DCM to give the title compound (105 mg). M.p. 170-1° C.

Workup

  1. customThe solvent was removed in vacuo
  2. washthe residue was washed with ether
  3. extractionextracted with DCM (thrice)
  4. dry with materialThe organic extracts were dried (MgSO4)
  5. customevaporated
  6. customcrystallised from isohexane—DCM

Sources & evidence

ORD record
ord-8eca094a94914f419a55e077fa534f7f
Source dataset
uspto-grants-2012_04
Patent number
US08163727B2

Reaction notes

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