Hydrochloric Acid → 5-(Isobutyryl-methyl-amino)-4'-methyl-biphenyl-3-carboxylic acid

HRID 2061719Notes

Reaction equation

HRID 2061719 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[C:7]([C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)[CH:8]=[C:9]([N:11]([C:13](=[O:17])[CH:14]([CH3:16])[CH3:15])[CH3:12])[CH:10]=1)=[O:4].[OH-].[Na+].Cl>CO>[C:13]([N:11]([CH3:12])[C:9]1[CH:10]=[C:5]([C:3]([OH:4])=[O:2])[CH:6]=[C:7]([C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)[CH:8]=1)(=[O:17])[CH:14]([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 14798Sodium HydroxideHCID 596275315-(Isobutyryl-methyl-amino)-4'-methyl-biphenyl-3-carboxylic acid methyl ester

Product 1

HCID 596275345-(Isobutyryl-methyl-amino)-4'-methyl-biphenyl-3-carboxylic acidYield 82.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-(Isobutyryl-methyl-amino)-4′-methyl-biphenyl-3-carboxylic acid methyl ester (85 mg, 0.26 mmol)) was added to a mixture of methanol (2 mL) and 1N aqueous NaOH (2 mL) and the mixture was stirred for one hour. HCl (1N aqueous solution) was added dropwise to the stirring solution until a precipitate formed. An additional 0.5 1M of 1N HCl was added, and the mixture was extracted with ethyl acetate. The combined organic extracts were washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure to give 67 mg of 5-(isobutyryl-methyl-amino)-4′-methyl-biphenyl-3-carboxylic acid.

Workup

  1. customformed
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3258570c225d4af3b4b7bf60e09a0fe0
Source dataset
uspto-grants-2012_10
Patent number
US08283383B2

Reaction notes

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