Hydrochloric Acid → ((1,1-Dimethylethyl)oxymethyl)-2'-fluoro-5'-(methyloxy)-1,1'-biphenyl-4-carboxylic acid

HRID 404375Notes

Reaction equation

HRID 404375 reaction equation
Br[CH2:2][C:3]1[CH:8]=[C:7]([C:9]([O:11]C)=[O:10])[CH:6]=[CH:5][C:4]=1[C:13]1[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[CH:15][C:14]=1[F:21].[CH3:22][C:23]([O-:26])([CH3:25])[CH3:24].[Na+].Cl>CN(C=O)C>[CH3:22][C:23]([O:26][CH2:2][C:3]1[CH:8]=[C:7]([C:9]([OH:11])=[O:10])[CH:6]=[CH:5][C:4]=1[C:13]1[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[CH:15][C:14]=1[F:21])([CH3:25])[CH3:24]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 23676156Sodium t-butoxideHCID 57705537Methyl 2-(bromomethyl)-2'-fluoro-5'-(methyloxy)-1,1'-biphenyl-4-carboxylate

Product 1

HCID 57705535((1,1-Dimethylethyl)oxymethyl)-2'-fluoro-5'-(methyloxy)-1,1'-biphenyl-4-carboxylic acidYield 20%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of T39.2 (0.245 g, 0.69 mmol) and sodium 2-methylpropan-2-olate (0.20 g, 2.1 mmol) in DMF (6 mL) was stirred at room temperature for 28 minutes. The mixture was acidified with 1N HCl to pH 3-4 and then was extracted with EtOAc (100 mL). The organic phase was washed with brine and dried over anhydrous Na2SO4. After removing solvent, the residue was purified by flash chromatography (silica gel, 1:4 EtOAc/hexane) and gave T39.3 (49 mg) in 20% yield.

Workup

  1. extractionwas extracted with EtOAc (100 mL)
  2. washThe organic phase was washed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. customAfter removing solvent
  5. customthe residue was purified by flash chromatography (silica gel, 1:4 EtOAc/hexane)
  6. customgave T39.3 (49 mg) in 20% yield

Sources & evidence

ORD record
ord-0af8127605f44c5e80c75cf44e7cf529
Source dataset
uspto-grants-2014_06
Patent number
US08748462B2

Reaction notes

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