Ethyl Acetate → Methyl 5-(4-cyanophenylamino)-3-methyl-5-oxopentanoate

HRID 2272562Notes

Reaction equation

HRID 2272562 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:18])[CH2:11][CH:12]([CH3:17])[CH2:13][C:14]([OH:16])=[O:15])=[CH:5][CH:4]=1)#[N:2].[C:19](OCC)(=O)C>S(=O)(=O)(O)O.CO>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:18])[CH2:11][CH:12]([CH3:17])[CH2:13][C:14]([O:16][CH3:19])=[O:15])=[CH:5][CH:4]=1)#[N:2]

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 3981627HCID 3981627, compound

Product 1

HCID 86729724Methyl 5-(4-cyanophenylamino)-3-methyl-5-oxopentanoateYield 56%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 887MethanolSolvent

Procedure

A solution of 5-(4-cyanophenylamino)-3-methyl-5-oxopentanoic acid (940 mg, 3.82 mmol) and conc. sulfuric acid (1 drop) in methanol (25 mL) was heated with reflux for 14 hr. The reaction solution was cooled, and ethyl acetate was added thereto. The solution was washed with water and saturated brine, and dried, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent gradient; 10 to 100% ethyl acetate/hexane) to give methyl 5-(4-cyanophenylamino)-3-methyl-5-oxopentanoate (557 mg, 2.139 mmol, 56.0%) as a white powder.

Workup

  1. temperaturewith reflux for 14 hr
  2. temperatureThe reaction solution was cooled
  3. washThe solution was washed with water and saturated brine
  4. customdried
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (solvent gradient; 10 to 100% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-1649ecf673174e2ea8250734fefab597
Source dataset
uspto-grants-2015_09
Patent number
US09120776B2

Reaction notes

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