Dimethyl oxalate → HCID 69477228, compound

HRID 2369838Notes

Reaction equation

HRID 2369838 reaction equation
[H-].[Na+].[C:3]([O:9][CH3:10])(=[O:8])[C:4](OC)=O.CC([N:15]([C:19]1[CH:24]=[CH:23][C:22]([C:25](=[O:27])C)=[CH:21][CH:20]=1)[C:16](=[O:18])[O-:17])(C)C>CN(C=O)C>[CH3:21][C:22]([O:17][C:16]([NH:15][C:19]1[CH:20]=[CH:21][C:22](/[C:25](/[OH:27])=[CH:4]/[C:3]([O:9][CH3:10])=[O:8])=[CH:23][CH:24]=1)=[O:18])([CH3:25])[CH3:23]

Participants

5

Reactant 3

HCID 11120Dimethyl oxalateHCID 24758Sodium hydrideHCID 86616954HCID 86616954, compound

Product 1

HCID 69477228HCID 69477228, compoundYield 111.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

NaH (60% dispersion, 2.22 g, 55.5 mmol) was added to a solution of dimethyl oxalate (2.73 g, 23.1 mmol) and 1,1-dimethylethyl(4-acetylphenyl)carbamate (N-BOC-4-aminoacetophenone, 5.44 g, 23.1 mmol) in anhydrous DMF (50 mL) at 0° C. The reaction mixture was allowed to warm to room temperature overnight and quenched with saturated aqueous NH4Cl and neutralized with 1M HCl. The reaction was diluted with ethyl acetate (80 mL) and the organic layer washed successively with saturated aqueous NaHCO3 and brine. The organic phase was separated and dried over Na2SO4, filtered, concentrated in vacuo and triturated with chloroform to provide the condensation product (3.77 g, 53.1% yield).

Workup

  1. customquenched with saturated aqueous NH4Cl and neutralized with 1M HCl
  2. additionThe reaction was diluted with ethyl acetate (80 mL)
  3. washthe organic layer washed successively with saturated aqueous NaHCO3 and brine
  4. customThe organic phase was separated
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customtriturated with chloroform

Sources & evidence

ORD record
ord-8aa525a2cd6943d69af0c5d909544e9e
Source dataset
uspto-grants-2014_04
Patent number
US08710038B2

Reaction notes

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