Acetamidomalonic acid diethyl ester → HCID 69428762, compound

HRID 1375917Notes

Reaction equation

HRID 1375917 reaction equation
[H-].[Na+].[O-]CC.[Na+].[CH2:7]([O:9][C:10](=[O:21])[CH:11]([NH:17][C:18](=[O:20])[CH3:19])[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH3:8].[C:22]1([C:28]2[CH:33]=[CH:32][C:31]([C:34](=[O:37])[CH2:35]Br)=[CH:30][CH:29]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(O)C>[CH2:15]([O:14][C:12](=[O:13])[C:11]([NH:17][C:18](=[O:20])[CH3:19])([CH2:35][C:34]([C:31]1[CH:32]=[CH:33][C:28]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:29][CH:30]=1)=[O:37])[C:10]([O:9][CH2:7][CH3:8])=[O:21])[CH3:16]

Participants

6

Reactant 4

HCID 14041Acetamidomalonic acid diethyl esterHCID 24758Sodium hydrideHCID 672821-(1,1'-Biphenyl)-4-yl-2-bromoethanoneHCID 2723922Sodium ethoxide

Product 1

HCID 69428762HCID 69428762, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Sodium hydride (15 mmol) is added to anhydrous ethanol (50 mL). To this resulting sodium ethoxide solution is added 2-acetylaminomalonic acid diethyl ester (15 mmol) in one portion. The resulting mixture is stirred at room temperature for 30 min. A solution of 4′-phenyl-2-bromoacetophenone (10 mmol) in ethanol (10 mL) is then added and the resulting mixture is stirred at room temperature for 12 h. After concentrating under reduced pressure, the residue is dissolved in EtOAc and water. The organic phase is washed with brine and dried over Na2SO4. After removal of the solvent, the crude material is purified by column chromatography using EtOAc/hexane (1/3) giving the desired product as white solid. 1H NMR (400 MHz, CDCl3) δ 8.03 (d, J=8.6 Hz, 2H), 7.68 (d, J=8.6 Hz, 2H), 7.61 (d, J=8.5 Hz, 2H), 7.45 (m, 3H), 7.13 (s, 1H), 4.28 (m, 6H), 1.98 (s, 2H), 1.26 (t, J=7.1 Hz, 6H); MS: (ES+): 412.2 (M+1)+.

Workup

  1. stirringthe resulting mixture is stirred at room temperature for 12 h
  2. concentrationAfter concentrating under reduced pressure
  3. dissolutionthe residue is dissolved in EtOAc
  4. washThe organic phase is washed with brine
  5. dry with materialdried over Na2SO4
  6. customAfter removal of the solvent
  7. customthe crude material is purified by column chromatography

Sources & evidence

ORD record
ord-209e9ee0f2214519a2c2673294153c11
Source dataset
uspto-grants-2007_01
Patent number
US07169817B2

Reaction notes

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