Sodium Hydroxide → HCID 68816292, compound

HRID 732538Notes

Reaction equation

HRID 732538 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-d9308d9d3a764353b0c204a9bba2ee79
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

Loading…