Acetamidomalonic acid diethyl ester → HCID 69196443, compound

HRID 32872Notes

Reaction equation

HRID 32872 reaction equation
[C:1]([NH:4][CH:5]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:6]([O:8][CH2:9][CH3:10])=[O:7])(=[O:3])[CH3:2].[H-].[Na+].[F:18][C:19]1[CH:24]=[CH:23][C:22]([C:25](Cl)(Cl)[C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=2)=[CH:21][CH:20]=1>CN(C)C=O.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:9]([O:8][C:6](=[O:7])[C:5]([NH:4][C:1](=[O:3])[CH3:2])([CH:25]([C:22]1[CH:23]=[CH:24][C:19]([F:18])=[CH:20][CH:21]=1)[C:26]1[CH:27]=[CH:28][C:29]([F:32])=[CH:30][CH:31]=1)[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH3:10]

Participants

6

Reactant 3

HCID 14041Acetamidomalonic acid diethyl esterHCID 24758Sodium hydrideHCID 12714043Bis(4-fluorophenyl)methylene chloride

Product 1

HCID 69196443HCID 69196443, compoundYield 76.8%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of diethyl acetamidomalonate (238 mg, 1.1 mmol) in N,N-dimethylformamide (1 mL) was added 55% sodium hydride (44 mg, 1.1 mmol), and the mixture was stirred at room temperature for 1 hr. Bis(4-fluorophenyl)methylene chloride (93 μL, 0.5 mmol) and tetra-n-butylammonium iodide (24 mg) were added, and the mixture was stirred at 50° C. for 16 hrs and then at 80° C. for 16 hrs. After completion of the reaction, HPLC quantitative analysis was performed to confirm 161 mg of the title compound (Inertsil ODS-2, 0.03 M phosphate buffer:acetonitrile=90:10-25:75 (20 min), 220 nm, 1.0 mL/min, rt).

Workup

  1. stirringthe mixture was stirred at 50° C. for 16 hrs
  2. waitat 80° C. for 16 hrs
  3. customAfter completion of the reaction, HPLC quantitative analysis

Sources & evidence

ORD record
ord-cdbc6185862641b7a4e553dfc455ca09
Source dataset
uspto-grants-2008_09
Patent number
US07427688B2

Reaction notes

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