Sodium Hydroxide → HCID 68816292, compound

HRID 1436680Notes

Reaction equation

HRID 1436680 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[C:7]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[F:24])[CH:8]=[C:9]([C:11](=[O:17])[N:12]([CH3:16])[CH2:13][CH2:14][CH3:15])[CH:10]=1)=[O:4].[OH-].[Na+]>CO.C1COCC1>[F:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[C:7]1[CH:8]=[C:9]([C:11](=[O:17])[N:12]([CH3:16])[CH2:13][CH2:14][CH3:15])[CH:10]=[C:5]([C:3]([OH:4])=[O:2])[CH:6]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 68814938HCID 68814938, compound

Product 1

HCID 68816292HCID 68816292, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Chill a solution of 2′-fluoro-5-(methyl-propylcarbamoyl)-biphenyl-3-carboxylic acid methyl ester (0.297 g, 0.903 mmol) in MeOH (2 mL) and THF (2 mL) in an ice bath. Add 2 N NaOH (1.35 mL, 2.70 mmol) to the mixture and stir at room temperature for 3 h. Acidify the solution to about pH=2 and concentrate to one half of the solvent. Partition the residue between ethyl acetate and H2O and extract the aqueous layer with ethyl acetate (2×15 mL). Wash the combined organic extract with saturated aqueous sodium chloride, dry (magnesium sulfate) and concentrate to give the title compound.

Workup

  1. concentrationconcentrate to one half of the solvent
  2. customPartition the residue between ethyl acetate and H2O
  3. extractionextract the aqueous layer with ethyl acetate (2×15 mL)
  4. washWash the combined
  5. extractionorganic extract with saturated aqueous sodium chloride
  6. dry with materialdry (magnesium sulfate)
  7. concentrationconcentrate

Sources & evidence

ORD record
ord-93c1af45ae734c07b8e6ef29bc867e75
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Reaction notes

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