Sodium ethoxide → HCID 15754168, compound

HRID 1461670Notes

Reaction equation

HRID 1461670 reaction equation
[Na].CC[O-].[Na+].[C:6]1([CH2:12][C:13]([N:15]([C:23]([CH3:31])([CH3:30])[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:16][CH2:17][C:18]([O:20]CC)=O)=[O:14])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>C(O)C>[CH3:30][C:23]([N:15]1[CH2:16][CH2:17][C:18](=[O:20])[CH:12]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:13]1=[O:14])([CH3:31])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 15754166HCID 15754166, compound

Product 1

HCID 15754168HCID 15754168, compoundYield 51.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

12.8 g of sodium metal was added to 500 ml of ethanol to prepare sodium ethylate, and 65.7 g (0.186 mol) of ethyl 3-(N-phenylacetyl-α,α-dimethylbenzylamino)propionate prepared by the method of Reference Example 17 was added thereto. The mixture was refluxed under heating for one hour. The reaction solution was cooled to room temperature, and then ethanol was distilled off under reduced pressure. The residue was poured into ice water and acidified with a 10% hydrochloric acid aqueous solution. Precipitated crystals were collected by filtration. The crude product thereby obtained was recrystallized from ethanol to obtain 29.5 g (yield: 51.6%) of the desired compound.

Workup

  1. customprepared by the method of Reference Example 17
  2. additionwas added
  3. temperatureThe mixture was refluxed
  4. temperatureunder heating for one hour
  5. distillationethanol was distilled off under reduced pressure
  6. additionThe residue was poured into ice water
  7. customPrecipitated crystals
  8. filtrationwere collected by filtration
  9. customThe crude product thereby obtained
  10. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-a602d317a70143dfa36d8032ab3af179
Source dataset
uspto-grants-1991_12
Patent number
US05076834

Reaction notes

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