m-Chloroperbenzoic acid → 3-[4-(2-Trifluoromethanesulfinyl-benzyloxy)-phenyl]-isoxazole-5-carboxylic acid amide

HRID 929769Notes

Reaction equation

[F:1][C:2]([S:5][C:6]1[CH:27]=[CH:26][CH:25]=[CH:24][C:7]=1[CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:20]=[C:19]([C:21]([NH2:23])=[O:22])[O:18][N:17]=2)=[CH:12][CH:11]=1)([F:4])[F:3].C1C=C(Cl)C=C(C(OO)=[O:36])C=1>C(Cl)Cl>[F:4][C:2]([F:1])([F:3])[S:5]([C:6]1[CH:27]=[CH:26][CH:25]=[CH:24][C:7]=1[CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:20]=[C:19]([C:21]([NH2:23])=[O:22])[O:18][N:17]=2)=[CH:12][CH:11]=1)=[O:36]

Participants

Conditions

Temperature: 0 °C

Procedure

A suspension of 3-[4-(2-trifluoromethylsulfanyl-benzyloxy)-phenyl]-isoxazole-5-carboxylic acid amide (which may be prepared as described in Example 1; 60 mg, 0.153 mmol) in CH2Cl2 (8 mL) was cooled to 0° C. in an ice-water bath. MCPBA (130 mg, 5 equivalents) was added and the mixture was stirred at 0° C. for 1 h and then at room temperature overnight. The reaction mixture was washed with 10% aqueous Na2SO3 and saturated aqueous NaHCO3, dried (Na2SO4), filtered, evaporated and purified by chromatography (35-45% EtOAc/hexanes) to give 3-[4-(2-trifluoromethanesulfinyl-benzyloxy)-phenyl]-isoxazole-5-carboxylic acid amide (16.2 mg, 26%) as a white solid. HRMS Calcd. for C18H14F3N2O4S (M+H)+, 411.0621. Found: 411.0617.

Workup

customat room temperature
customovernight
washThe reaction mixture was washed with 10% aqueous Na2SO3 and saturated aqueous NaHCO3
dry with materialdried (Na2SO4)
filtrationfiltered
customevaporated
custompurified by chromatography (35-45% EtOAc/hexanes)

Sources & evidence

ORD record: ord-c4291eb393c046b89ac26aaf2f9d4fb2
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296711B2

Reaction notes

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