Water → Methyl 5-(benzyl(4-cyanophenyl)amino)-3-methyl-5-oxopentanoate

HRID 2272563Notes

Reaction equation

HRID 2272563 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:19])[CH2:11][CH:12]([CH3:18])[CH2:13][C:14]([O:16][CH3:17])=[O:15])=[CH:5][CH:4]=1)#[N:2].[H-].[Na+].[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.O>CN(C=O)C>[CH2:22]([N:9]([C:6]1[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][CH:7]=1)[C:10](=[O:19])[CH2:11][CH:12]([CH3:18])[CH2:13][C:14]([O:16][CH3:17])=[O:15])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 86729724Methyl 5-(4-cyanophenylamino)-3-methyl-5-oxopentanoate

Product 1

HCID 86729725Methyl 5-(benzyl(4-cyanophenyl)amino)-3-methyl-5-oxopentanoateYield 26.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the compound obtained in Step 1 (228 mg, 0.88 mmol) in DMF (6 mL) was added sodium hydride (60% in oil, 126 mg, 2.63 mmol) at 0° C. The reaction mixture was stirred at room temperature for 30 min, and benzyl bromide (0.156 mL, 1.31 mmol) was added thereto at 0° C. The reaction mixture was stirred at room temperature for 14 hr, to the reaction solution was added water, 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. The obtained residue was purified by silica gel column chromatography (solvent gradient; 5 to 85% ethyl acetate/hexane) to give methyl 5-(benzyl(4-cyanophenyl)amino)-3-methyl-5-oxopentanoate (81 mg, 0.230 mmol, 26.3%) as a colorless oil.

Workup

  1. customat 0° C
  2. stirringThe reaction mixture was stirred at room temperature for 14 hr, to the reaction solution
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with water and saturated brine
  5. customdried
  6. customthe solvent was evaporated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (solvent gradient; 5 to 85% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-cc8b7c69b4c24364ab9150c3f12c0d7f
Source dataset
uspto-grants-2015_09
Patent number
US09120776B2

Reaction notes

Loading…