Acetamidomalonic acid diethyl ester → HCID 67246761, compound

HRID 2425317Notes

Reaction equation

HRID 2425317 reaction equation
[H-].[Na+].[C:3]([NH:6][CH:7]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:8]([O:10][CH2:11][CH3:12])=[O:9])(=[O:5])[CH3:4].Br[CH:19]1[CH2:27][C:26]2[C:21](=[CH:22][CH:23]=[C:24]([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH:25]=2)[C:20]1=[O:36]>CN(C=O)C>[CH2:11]([O:10][C:8](=[O:9])[C:7]([NH:6][C:3](=[O:5])[CH3:4])([CH:19]1[CH2:27][C:26]2[C:21](=[CH:22][CH:23]=[C:24]([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH:25]=2)[C:20]1=[O:36])[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH3:12]

Participants

5

Reactant 3

HCID 14041Acetamidomalonic acid diethyl esterHCID 24758Sodium hydrideHCID 67246500HCID 67246500, compound

Product 1

HCID 67246761HCID 67246761, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a stirring solution of 60% NaH (1.194 g, 29.85 mmol) in DMF (5 mL) was added diethyl acetamidomalonate (6.484 g, 29.85 mmol) via cannula at 0° C. The solution was allowed to stir for 3 hours for anion to form. A solution of 3 (3.22 g, 9.95 mmol) in DMF (10 mL) was then added to then transferred to anion solution at 0° C. and left to stir over night at room temp. The reaction mixture was then poured over ice and extracted with EtOAc. The organic layer was washed with brine, dried with NaSO4 and concentrated. The product was then purified with silica gel chromatography eluding with 70% hexanes-30% EtOAc. The reaction provided 4 (2.842 g, 6.184 mmol, 65%).

Workup

  1. customto form
  2. customto then transferred to anion solution at 0° C.
  3. waitleft
  4. stirringto stir over night at room temp
  5. additionThe reaction mixture was then poured over ice
  6. extractionextracted with EtOAc
  7. washThe organic layer was washed with brine
  8. dry with materialdried with NaSO4
  9. concentrationconcentrated
  10. customThe product was then purified with silica gel chromatography

Sources & evidence

ORD record
ord-c28649fa061e44d7a9d042c489596b51
Source dataset
uspto-grants-2011_06
Patent number
US07964649B2

Reaction notes

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