Phosphate → HCID 20074982, compound

HRID 703822Notes

Reaction equation

HRID 703822 reaction equation
[CH3:1][NH:2][C:3]([NH:5][N:6]([CH2:16][C:17]([O:19]C)=O)[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH2:13][CH2:14][CH3:15])[CH:8]=1)=[O:4].C[O-].[Na+].P([O-])([O-])([O-])=O>CO>[CH3:1][N:2]1[C:17](=[O:19])[CH2:16][N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([CH2:13][CH2:14][CH3:15])[CH:8]=2)[NH:5][C:3]1=[O:4]

Participants

5

Reactant 3

HCID 1061PhosphateHCID 10942334Sodium MethoxideHCID 54113410Methyl [2-[(methylamino)carbonyl]-1-(3-propylphenyl)hydrazino]acetate

Product 1

HCID 20074982HCID 20074982, compoundYield 34.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl [2-[(methylamino)carbonyl]-1-(3-propylphenyl)hydrazino]acetate (0.5 g) was dissolved in methanol (20 ml) under nitrogen at room temperature. Solid sodium methoxide (0.24 g) was added to the solution which was then stirred at room temperature for 1 h. The reaction mixture was poured into pH 6.5 phosphate buffer solution (10 ml) and extracted with ethyl acetate (3×30 ml). The combined, dried organic phases were concentrated in vacuo and the residual oil was purified by FCC eluting with chloroform:ether (95:5) to give a solid (152 mg) which was triturated with ether to give the title compound (90 mg), m.p. 112°-115°.

Workup

  1. extractionextracted with ethyl acetate (3×30 ml)
  2. concentrationdried organic phases were concentrated in vacuo
  3. customthe residual oil was purified by FCC
  4. washeluting with chloroform:ether (95:5)

Sources & evidence

ORD record
ord-c0c595b0b117489e8a179440c7ec419a
Source dataset
uspto-grants-1991_01
Patent number
US04985427

Reaction notes

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