m-Chloroperbenzoic acid → HCID 11684520, compound

HRID 892255Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]2[O:11][CH:12]=[C:13]([CH2:15][O:16][C:17]3[CH:31]=[CH:30][C:20]([CH2:21][S:22][CH2:23][CH2:24][N:25]4[CH:29]=[CH:28][N:27]=[N:26]4)=[CH:19][CH:18]=3)[N:14]=2)=[C:4]([F:32])[CH:3]=1.ClC1C=C(C(OO)=[O:41])C=CC=1>ClCCl.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]2[O:11][CH:12]=[C:13]([CH2:15][O:16][C:17]3[CH:31]=[CH:30][C:20]([CH2:21][S:22]([CH2:23][CH2:24][N:25]4[CH:29]=[CH:28][N:27]=[N:26]4)=[O:41])=[CH:19][CH:18]=3)[N:14]=2)=[C:4]([F:32])[CH:3]=1

Participants

Conditions

Temperature: 30 °C

Procedure

To a solution of 320 mg (0.68 mmol) 1-[2-(4-{2-[2-(E)-(4-chloro-2-fluoro-phenyl)vinyl]-oxazol-4-ylmethoxy}-benzylsulfanyl)-ethyl]-1H-[1,2,3]triazole in 9 ml dichloromethane at −30° C. were added dropwise during 20 min 197 mg (0.88 mmol) 3-chloro-benzenecarboperoxoic acid dissolved in 9 ml ethyl acetate. After 1 hour stirring at 30° C. the mixture was allowed to warm up over night, stirred another 48 hours at room temperature, diluted with dichloromethane, washed with sodium bicarbonate solution, then with water, dried and evaporated. Elution from silica with ethyl acetate/methanol 20:1 furnished as the second fraction 171 mg (51%) title compound as white solid.

Workup

temperatureto warm up over night
stirringstirred another 48 hours at room temperature
washwashed with sodium bicarbonate solution
dry with materialwith water, dried
customevaporated
washElution from silica with ethyl acetate/methanol 20:1

Sources & evidence

ORD record: ord-548f1051948f4d969012100b18cbb9fa
Source dataset: uspto-grants-2006_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07005526B2

Reaction notes

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