HCID 67107992, compound → HCID 67107596, compound

HRID 2177723Notes

Reaction equation

HRID 2177723 reaction equation
[C:1]1([S:7]([CH2:10][C:11]2[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:15]([O:22][CH3:23])[C:14]([C:24]3[CH2:28][CH:27](O)[O:26][N:25]=3)=[CH:13][CH:12]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C(O)C>[C:1]1([S:7]([CH2:10][C:11]2[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:15]([O:22][CH3:23])[C:14]([C:24]3[CH:28]=[CH:27][O:26][N:25]=3)=[CH:13][CH:12]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 1

HCID 67107992HCID 67107992, compound2×

Product 1

HCID 67107596HCID 67107596, compoundYield 76.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
140 °C

Procedure

A solution of ethyl 6-(benzenesulphonylmethyl)-3-(5-hydroxy-4,5-dihydroisoxazol-3-yl)-2-methoxybenzoate (Intermediate 49, 0.041 g) in ethanol (3 ml) was stirred and heated in the microwave at 140° C. for 15 minutes then at 160° C. for 75 minutes. After cooling, the solution was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-50% to give ethyl 6-(benzenesulphonylmethyl)-3-(isoxazol-3-yl)-2-methoxybenzoate (0.03 g) as a gum.

Workup

  1. temperatureAfter cooling
  2. customthe solution was evaporated to dryness
  3. customthe residue was purified by chromatography on silica
  4. washeluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-50%

Sources & evidence

ORD record
ord-613e57812f92470b96d0058e0e728ac1
Source dataset
uspto-grants-2015_06
Patent number
US09067905B2

Reaction notes

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