Methanol → HCID 54692130, compound

HRID 1084641Notes

Reaction equation

HRID 1084641 reaction equation
[C:1]1([CH2:7][C:8]([N:10]([C:16]([CH3:24])([CH3:23])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:11][C:12](OC)=[O:13])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CO.C[O-].[Na+]>C(O)C>[CH3:23][C:16]([N:10]1[CH2:11][C:12]([OH:13])=[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:8]1=[O:9])([CH3:24])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 10942334Sodium MethoxideHCID 15754164HCID 15754164, compound

Product 1

HCID 54692130HCID 54692130, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

10 g (30 mmol) of methyl 2-(N-phenylacetyl-α,α-dimethylbenzylamino)acetate was dissolved in 100 ml of ethanol, and 17.4 g (90 mmol) of a methanol solution of 28% sodium methylate was added thereto. The mixture was refluxed under heating for 0.5 hour. The reaction solvent was distilled off under reduced pressure, and the residue was poured into ice water and acidified with 10% hydrochloric acid. Precipitated crude crystals were collected by filtration and recrystallized from ethanol to obtain 4.0 g (yield: 46%) of the desired compound.

Workup

  1. temperatureThe mixture was refluxed
  2. temperatureunder heating for 0.5 hour
  3. distillationThe reaction solvent was distilled off under reduced pressure
  4. additionthe residue was poured into ice water
  5. customPrecipitated crude crystals
  6. filtrationwere collected by filtration
  7. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-398bdab89a5f417487daee95cc6645a7
Source dataset
uspto-grants-1991_04
Patent number
US05006157

Reaction notes

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