Methyl Benzoate → HCID 178452749, compound

HRID 2369832Notes

Reaction equation

HRID 2369832 reaction equation
[H-].[Na+].[C:3](OC)(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:13]([C:16]1[CH:21]=[CH:20][C:19]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[CH:18][CH:17]=1)(=[O:15])[CH3:14]>CN(C=O)C>[OH:15]/[C:13](/[C:16]1[CH:17]=[CH:18][C:19]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[CH:20][CH:21]=1)=[CH:14]\[C:3](=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 7150Methyl BenzoateHCID 24758Sodium hydrideHCID 15373979tert-Butyl (4-acetylphenyl)carbamate

Product 1

HCID 178452749HCID 178452749, compoundYield 83.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

NaH (60% dispersion, 0.388 g, 16.2 mmol) was added to a solution of methyl benzoate (0.629 g, 4.62 mmol) and 1,1-dimethylethyl (4-acetylphenyl)carbamate (N-BOC-4-aminoacetophenone 1.09 g, 4.62 mmol) in anhydrous DMF (20 mL) at 0° C. The reaction was allowed to warm to room temperature overnight then 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, and concentrated in vacuo to provide the condensation product as a yellow oil (1.31 g, 83% yield). The product was used in the subsequent step without further purification.

Workup

  1. customthen quenched 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

Sources & evidence

ORD record
ord-a1e706f2a72d4e50ac972fff794bf634
Source dataset
uspto-grants-2014_04
Patent number
US08710038B2

Reaction notes

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