Sodium Methoxide → HCID 19829820, compound

HRID 1493645Notes

Reaction equation

HRID 1493645 reaction equation
[NH2:1][C:2]([NH:4][N:5]([CH2:15][C:16]([O:18]C)=O)[C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([CH3:14])[CH:7]=1)=[O:3].C[O-].[Na+]>CO.C(OCC)(=O)C>[CH3:13][O:12][C:9]1[CH:10]=[CH:11][C:6]([N:5]2[CH2:15][C:16](=[O:18])[NH:1][C:2](=[O:3])[NH:4]2)=[CH:7][C:8]=1[CH3:14]

Participants

5

Reactant 2

HCID 10942334Sodium Methoxide3×HCID 53963885HCID 53963885, compound2×

Product 1

HCID 19829820HCID 19829820, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl [2-[aminocarbonyl]-1-[4-methoxy-3-methyl phenyl]hydrazino]acetate (Intermediate 98, 222 mg, 0.8 mmol) in methanol (5 ml) was added sodium methoxide (43 mg, 0.8 mmol) with stirring and under nitrogen. After 30 minutes further sodium methoxide (43 mg, 0.8 mmol) was added and the reaction stirred at room temperature for 14 hours. Three separate portions of sodium methoxide (43 mg, 0.8 mmol) were then added with 30 minutes between each before the reaction was poured into pH 6 buffer (30 ml) and extracted with ethyl acetate (2×25 ml). The organic extract was dried (MgSO4) and evaporated to give a white semi-solid which was triturated with ethylacetate-ether (~1:1) to give an off white solid. This was dissolved in ethyl acetate (10 ml), filtered and evaporated to give the title compound as an off white solid (18 mg, 10%) m.p. 220°-222° C. (decomp).

Workup

  1. stirringthe reaction stirred at room temperature for 14 hours
  2. additionwere then added with 30 minutes between each before the reaction
  3. additionwas poured into pH 6 buffer (30 ml)
  4. extractionextracted with ethyl acetate (2×25 ml)
  5. extractionThe organic extract
  6. dry with materialwas dried (MgSO4)
  7. customevaporated
  8. customto give a white semi-solid which
  9. customwas triturated with ethylacetate-ether (~1:1)
  10. customto give an off white solid
  11. filtrationfiltered
  12. customevaporated

Sources & evidence

ORD record
ord-37219ee669a84e308c2ab557cd600079
Source dataset
uspto-grants-1991_06
Patent number
US05023255

Reaction notes

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