Potassium caroate → HCID 16722419, compound

HRID 2421196Notes

Reaction equation

HRID 2421196 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([C:8]2[O:9][C:10]([C:13]3[C:14]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)=[N:15][O:16][C:17]=3[CH3:18])=[N:11][N:12]=2)[C:5]([O:25][CH3:26])=[CH:4][C:3]=1[N:27]1[CH2:32][CH2:31]S[CH2:29][CH2:28]1.[OH:33][S:34]([O-:37])(=O)=O.OS(O[O-])(=O)=O.OS(O[O-])(=O)=O.[O-]S([O-])(=O)=O.[K+].[K+].[K+].[K+].[K+].S(=O)(O)[O-].[Na+]>CO.O>[F:1][C:2]1[CH:7]=[C:6]([C:8]2[O:9][C:10]([C:13]3[C:14]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)=[N:15][O:16][C:17]=3[CH3:18])=[N:11][N:12]=2)[C:5]([O:25][CH3:26])=[CH:4][C:3]=1[N:27]1[CH2:32][CH2:31][S:34](=[O:37])(=[O:33])[CH2:29][CH2:28]1

Participants

6

Reactant 3

HCID 15793144Potassium caroateHCID 16722363HCID 16722363, compoundHCID 23665763Sodium Bisulfite

Product 1

HCID 16722419HCID 16722419, compoundYield 53.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of 4-{2-fluoro-5-methoxy-4-[5-(5-methyl-3-phenyl-isoxazol-4-yl)-[1,3,4]oxadiazol-2-yl]-phenyl}-thiomorpholine (400 mg, 0.88 mmol) in methanol (6 mL) and water (0.3 mL) was added potassium monopersulfate triple salt (1.09 g, 1.77 mmol) under an atmosphere of nitrogen and the mixture was heated for 18 h at 80° C. The reaction mixture was cooled to ambient temperature, sodium bisulfite (38% in water, 3 mL) was added and stirred for 0.5 h at ambient temperature. The resulting suspension was extracted with dichloromethane (20 mL) and washed with aqueous sodium carbonate (half saturated). Drying over sodium sulfate and purification by chromatography (SiO2, heptane:ethyl acetate:dichloromethane=40:40:20 to 10:70:20) afforded the title compound (228 mg, 53%) as a white solid. MS: m/e=485.3 [M+H]+.

Workup

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. extractionThe resulting suspension was extracted with dichloromethane (20 mL)
  3. washwashed with aqueous sodium carbonate (half saturated)
  4. dry with materialDrying over sodium sulfate and purification by chromatography (SiO2, heptane:ethyl acetate:dichloromethane=40:40:20 to 10:70:20)

Sources & evidence

ORD record
ord-54363848ba7a4fba8d2cc4e231c3cd37
Source dataset
uspto-grants-2011_06
Patent number
US07956074B2

Reaction notes

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