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

HRID 340619Notes

Reaction equation

HRID 340619 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 lM 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-df43d745f18d4ea3a93ce2bc69348e8a
Source dataset
uspto-grants-2014_11
Patent number
US08895589B2

Reaction notes

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