m-Chloroperbenzoic acid → HCID 11663363, compound

HRID 892262Notes

Reaction equation

[CH3:1][C:2]1[CH:16]=[C:15]([O:17][CH2:18][C:19]2[N:20]=[C:21](/[CH:24]=[CH:25]/[C:26]3[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][C:27]=3[F:33])[O:22][CH:23]=2)[CH:14]=[CH:13][C:3]=1[CH2:4][S:5][CH2:6][CH2:7][N:8]1[CH:12]=[CH:11][N:10]=[N:9]1.ClC1C=CC=C(C(OO)=[O:42])C=1>ClCCl.C(OCC)(=O)C>[Cl:32][C:29]1[CH:30]=[CH:31][C:26](/[CH:25]=[CH:24]/[C:21]2[O:22][CH:23]=[C:19]([CH2:18][O:17][C:15]3[CH:14]=[CH:13][C:3]([CH2:4][S:5]([CH2:6][CH2:7][N:8]4[CH:12]=[CH:11][N:10]=[N:9]4)=[O:42])=[C:2]([CH3:1])[CH:16]=3)[N:20]=2)=[C:27]([F:33])[CH:28]=1

Participants

Conditions

Temperature: -30 °C

Procedure

To a solution of 710 mg (1.46 mmol) 1-[2-(2-methyl-4-{2-[2-(E)-(4-chloro-2-fluorophenyl)-vinyl]-oxazol-4-ylmethoxy}-benzylsulfanyl)-ethyl]-1H-[1,2,3]triazole in 35 ml dichloromethane at −30° C. were added dropwise during 20 min. 493 mg (2.20 mmol) 3-chloro-perbenzoic acid (77% peracid) dissolved in 20 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 (1–10% methanol gradient) gave as the second fraction 199 mg (27%) 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 (1–10% methanol gradient)

Sources & evidence

ORD record: ord-223b2c39c86c404ea7490b010264805b
Source dataset: uspto-grants-2006_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07005526B2

Reaction notes

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