Citric Acid → HCID 11553414, compound

HRID 1169946Notes

Reaction equation

HRID 1169946 reaction equation
C[O:2][C:3](=[O:31])[C:4]([C:7]1[CH:8]=[C:9]([C:21]2[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=2)[CH:10]=[C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:12]=1)([CH3:6])[CH3:5].[OH-].[K+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1.CO.O>[CH2:14]([O:13][C:11]1[CH:12]=[C:7]([C:4]([CH3:6])([CH3:5])[C:3]([OH:31])=[O:2])[CH:8]=[C:9]([C:21]2[CH:26]=[CH:25][C:24]([C:27]([F:29])([F:30])[F:28])=[CH:23][CH:22]=2)[CH:10]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

7

Reactant 3

HCID 311Citric AcidHCID 14797Potassium HydroxideHCID 68694659HCID 68694659, compound

Product 1

HCID 11553414HCID 11553414, compoundYield 39.3%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-(5-benzyloxy-4′-trifluoromethyl-biphenyl-3-yl)-2-methyl-propionic acid methyl ester (0.12 g, 0.28 mmol) in THF (4 ml) was treated at room temperature with a solution of KOH (0.17 g, 3.00 mmol) in methanol and water (3 ml, 6:1). After two days the mixture was acidified with citric acid and extracted with EtOAc. The combined organic extracts were washed with NaHCO3 solution (sat aq), brine, dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by flash column chromatography (EtOAc:petroleum ether) to give 2-(5-benzyloxy-4′-trifluoromethyl-biphenyl-3-yl)-2-methyl-propionic acid (0.045 g, 0.11 mmol) as a white solid in 39% yield. 1H NMR (d4-MeOD) 7.79-7.71 (m, 4H), 7.50-7.46 (m, 2H), 7.42-7.36 (m, 2H), 7.35-7.29 (m, 1H), 7.25-7.23 (m, 1H), 7.17-7.14 (m, 1H), 7.08-7.05 (m, 1H), 5.17 (s, 2H), 1.59 (s, 6H); LCMS method (A), RT=4.5 min.

Workup

  1. extractionextracted with EtOAc
  2. washThe combined organic extracts were washed with NaHCO3 solution (sat aq), brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash column chromatography (EtOAc:petroleum ether)

Sources & evidence

ORD record
ord-9c7889d0a11f4d23a93fe7ed78bdd9ae
Source dataset
uspto-grants-2010_11
Patent number
US07825160B2

Reaction notes

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