m-Chloroperbenzoic acid → HCID 22475017, compound

HRID 2103131Notes

Reaction equation

ClC1C=CC=C(C(OO)=[O:9])C=1.[Cl:12][C:13]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=1[C:20]1([C:38]2[CH:43]=[CH:42][C:41]([F:44])=[CH:40][CH:39]=2)[O:24][C:23]2[CH:25]=[C:26]([F:37])[C:27]([C:29]([N:31]3[CH2:36][CH2:35][S:34][CH2:33][CH2:32]3)=[O:30])=[CH:28][C:22]=2[O:21]1>ClCCl>[Cl:12][C:13]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=1[C:20]1([C:38]2[CH:43]=[CH:42][C:41]([F:44])=[CH:40][CH:39]=2)[O:24][C:23]2[CH:25]=[C:26]([F:37])[C:27]([C:29]([N:31]3[CH2:36][CH2:35][S:34](=[O:9])[CH2:33][CH2:32]3)=[O:30])=[CH:28][C:22]=2[O:21]1

Participants

Conditions

Temperature: -20 °C

Procedure

A solution of m-chloroperbenzoic acid (74 mg, 0.3 mmol) in dichloromethane (1.2 mL) was added to a cooled (−20° C.) solution of [2-(2,4-Dichloro-phenyl)-6-fluoro-2-(4-fluoro-phenyl)-benzo[1,3]dioxol-5-yl]-thiomorpholin-4-yl-methanone (Example 136) (153 mg, 0.3 mmol) in dichloromethane (1.7 mL). The reaction mixture was stirred at −20° C. for 3 h, quenched with 5% aqueous sodium thiosulfate solution. The aqueous phase was extracted with dichloromethane and the combined organic phases were washed with 10% sodium bicarbonate solution and brine, dried over sodium sulfate, filtered and the volatiles were removed under vacuo. Purification by flash chromatography afforded the title product as a white foam (141 mg, 89%).

Workup

customquenched with 5% aqueous sodium thiosulfate solution
extractionThe aqueous phase was extracted with dichloromethane
washthe combined organic phases were washed with 10% sodium bicarbonate solution and brine
dry with materialdried over sodium sulfate
filtrationfiltered
customthe volatiles were removed under vacuo
customPurification by flash chromatography

Sources & evidence

ORD record: ord-37875c4ea0064a9696814d06e2402181
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07576088B2

Reaction notes

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