Acetamidomalonic acid diethyl ester → Diethyl 2-acetylamino-2-(4-methyl-4-nitropentyl)malonate

HRID 432992Notes

Reaction equation

HRID 432992 reaction equation
[O-]CC.[Na+].[C:5]([NH:8][CH:9]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:10]([O:12][CH2:13][CH3:14])=[O:11])(=[O:7])[CH3:6].[CH3:20][C:21]([N+:27]([O-:29])=[O:28])([CH3:26])[CH2:22][CH2:23][CH2:24]I>C(O)C>[C:5]([NH:8][C:9]([CH2:24][CH2:23][CH2:22][C:21]([CH3:26])([N+:27]([O-:29])=[O:28])[CH3:20])([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:10]([O:12][CH2:13][CH3:14])=[O:11])(=[O:7])[CH3:6]

Participants

5

Reactant 3

HCID 14041Acetamidomalonic acid diethyl esterHCID 2723922Sodium ethoxideHCID 99430631-Iodo-4-methyl-4-nitro-pentane

Product 1

HCID 9968068Diethyl 2-acetylamino-2-(4-methyl-4-nitropentyl)malonateYield 83.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

20% Sodium ethoxide (3.74 g, 11 mmol) and diethyl 2-acetamidomalonate (2.39 g, 11 mmol) were dissolved in ethanol (10 ml). A solution of 4-methyl-4-nitropentyl iodide (2.57 g, 10 mmol) in ethanol (8 ml) was added and the mixture was refluxed under heating for 5 h. Ethanol was evaporated by concentration under reduced pressure and ethyl acetate (50 ml) was added. The mixture was washed with water (20 ml) and saturated brine (20 ml). Ethyl acetate was evaporated by concentration under reduced pressure and the residue was purified by silica gel column chromatography to give the objective compound (2.89 g, yield 83.4%).

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 5 h
  3. customEthanol was evaporated by concentration under reduced pressure and ethyl acetate (50 ml)
  4. additionwas added
  5. washThe mixture was washed with water (20 ml) and saturated brine (20 ml)
  6. customEthyl acetate was evaporated by concentration under reduced pressure
  7. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-17ca81093ca44bfaab46202d2c4bf367
Source dataset
uspto-grants-2003_12
Patent number
US06664412B2

Reaction notes

Loading…