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

HRID 16080Notes

Reaction equation

HRID 16080 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].C1COCC1.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

5

Reactant 3

HCID 887MethanolHCID 8028TetrahydrofuranHCID 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), THF (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-1337c7f227634bcd8df85a5cdcb4d3ad
Source dataset
uspto-grants-2010_06
Patent number
US07737135B2

Reaction notes

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