Sodium Methoxide → HCID 67110120, compound

HRID 409226Notes

Reaction equation

HRID 409226 reaction equation
C[O:2][C:3](=O)[C:4]1[C:9]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:17][N:18]([CH2:29][C:30]([O:32][CH3:33])=[O:31])S(C1C=CC(C)=CC=1)(=O)=O.C[O-].[Na+]>CO>[CH3:33][O:32][C:30]([C:29]1[N:18]=[CH:17][C:5]2[C:4]([C:3]=1[OH:2])=[C:9]([O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH:8]=[CH:7][CH:6]=2)=[O:31]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 67110387HCID 67110387, compound

Product 1

HCID 67110120HCID 67110120, compoundYield 26.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of crude 2-{[Methoxycarbonylmethyl-(toluene-4-sulfonyl)-amino]-methyl}-6-phenoxy-benzoic acid methyl ester (3.87 g) in methanol (24 mL) was added a solution of NaOMe (30 wt %) in methanol (4 mL) with stirring. After stirring for 3 days at ambient temperature the mixture was concentrated in vacuo. To the residue was added 1 N hydrochloric acid (20 mL) and the mixture was extracted with ethyl acetate (1×100 mL). The organic phase was then washed with concentrated aqueous NaHCO3 solution (3×100 mL), dried over MgSO4 and concentrated in vacuo. The residue was recrystallized from ethyl acetate to give the title compound as a yellowish solid (630 mg); MS-(+)-ion: M+1=295.8.

Workup

  1. stirringAfter stirring for 3 days at ambient temperature the mixture
  2. concentrationwas concentrated in vacuo
  3. additionTo the residue was added 1 N hydrochloric acid (20 mL)
  4. extractionthe mixture was extracted with ethyl acetate (1×100 mL)
  5. washThe organic phase was then washed with concentrated aqueous NaHCO3 solution (3×100 mL)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-13fbc19034ef47d69b02be287a92bc2e
Source dataset
uspto-grants-2014_06
Patent number
US08759373B2

Reaction notes

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