Sodium Methoxide → HCID 24855871, compound

HRID 545323Notes

Reaction equation

HRID 545323 reaction equation
[C:1]([C:5]1[O:9][N:8]=[C:7]([NH:10][C:11](=[O:25])[C:12]([S:15]([C:18]2[CH:19]=[N:20][C:21](Cl)=[CH:22][CH:23]=2)(=[O:17])=[O:16])([CH3:14])[CH3:13])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:26][O-:27].[Na+]>CO>[C:1]([C:5]1[O:9][N:8]=[C:7]([NH:10][C:11](=[O:25])[C:12]([S:15]([C:18]2[CH:19]=[N:20][C:21]([O:27][CH3:26])=[CH:22][CH:23]=2)(=[O:17])=[O:16])([CH3:14])[CH3:13])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 24855869HCID 24855869, compound

Product 1

HCID 24855871HCID 24855871, compoundYield 31.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 115 mg (0.30 mmol) N-(5-tert-butyl-isoxazol-3-yl)-2-(6-chloro-pyridine-3-sulfonyl)-2-methyl-propionamide in methanol (3 mL) were added 0.14 mL (0.6 mmol, 25 wt % solution in methanol) of sodium methoxide solution. The reaction mixture was heated in a sealed tube to 60° C. for 4 h. The solution was concentrated under reduced pressure and the residue purified by column chromatography (silica, eluent DCM, 0-20% ethyl acetate) to afford 36 mg of N-(5-tert-butyl-isoxazol-3-yl)-2-(6-methoxy-pyridine-3-sulfonyl)-2-methyl-propionamide.

Workup

  1. concentrationThe solution was concentrated under reduced pressure
  2. customthe residue purified by column chromatography (silica, eluent DCM, 0-20% ethyl acetate)

Sources & evidence

ORD record
ord-0c3ec30436904e4b86a09fe3ae56a1f2
Source dataset
uspto-grants-2011_05
Patent number
US07935715B2

Reaction notes

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