Hydrochloric Acid → 5-(Benzyl(4-cyanophenyl)amino)-3-methyl-5-oxopentanoic acid

HRID 2272564Notes

Reaction equation

HRID 2272564 reaction equation
[CH2:1]([N:8]([C:19]1[CH:24]=[CH:23][C:22]([C:25]#[N:26])=[CH:21][CH:20]=1)[C:9](=[O:18])[CH2:10][CH:11]([CH3:17])[CH2:12][C:13]([O:15]C)=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].Cl>CO.C1COCC1>[CH2:1]([N:8]([C:19]1[CH:24]=[CH:23][C:22]([C:25]#[N:26])=[CH:21][CH:20]=1)[C:9](=[O:18])[CH2:10][CH:11]([CH3:17])[CH2:12][C:13]([OH:15])=[O:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86729725Methyl 5-(benzyl(4-cyanophenyl)amino)-3-methyl-5-oxopentanoate

Product 1

HCID 867297265-(Benzyl(4-cyanophenyl)amino)-3-methyl-5-oxopentanoic acidYield 97%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of the compound obtained in Step 2 (80.0 mg, 0.23 mmol) and 1N aqueous sodium hydroxide solution (1 mL, 1.00 mmol) in methanol (2 mL) and THF (2 mL) was stirred at room temperature for 14 hr. The reaction solution was neutralized with 1N hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried, and the solvent was evaporated under reduced pressure to give crude 5-(benzyl(4-cyanophenyl)amino)-3-methyl-5-oxopentanoic acid (74.2 mg, 0.221 mmol, 97%) as a white powder.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. customdried
  4. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-f7bf79098e034890a051f3639615d4ac
Source dataset
uspto-grants-2015_09
Patent number
US09120776B2

Reaction notes

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