m-Chloroperbenzoic acid → 4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-[2-(methylsulfinyl)ethyl]-1-naphthalenecarboxamide

HRID 467592Notes

Reaction equation

ClC1C=C(C2(C(F)(F)F)ON=C(C3C4C(=CC=CC=4)C(C(NCCSC)=O)=CC=3)C2)C=C(Cl)C=1.[Cl:35][C:36]1[CH:37]=[C:38]([C:43]2([C:73]([F:76])([F:75])[F:74])[O:47][N:46]=[C:45]([C:48]3[C:57]4[C:52](=[CH:53][CH:54]=[CH:55][CH:56]=4)[C:51]([C:58]([NH:60][CH2:61][CH2:62][S:63]([CH3:72])(=NC(=O)C(F)(F)F)=[O:64])=[O:59])=[CH:50][CH:49]=3)[CH2:44]2)[CH:39]=[C:40]([Cl:42])[CH:41]=1.C1C=C(Cl)C=C(C(OO)=O)C=1>ClCCl>[Cl:42][C:40]1[CH:39]=[C:38]([C:43]2([C:73]([F:74])([F:76])[F:75])[O:47][N:46]=[C:45]([C:48]3[C:57]4[C:52](=[CH:53][CH:54]=[CH:55][CH:56]=4)[C:51]([C:58]([NH:60][CH2:61][CH2:62][S:63]([CH3:72])=[O:64])=[O:59])=[CH:50][CH:49]=3)[CH2:44]2)[CH:37]=[C:36]([Cl:35])[CH:41]=1

Participants

Conditions

Temperature: -74 °C

Procedure

To a stirred solution of 4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-[2-(methylthio)ethyl]-1-naphthalenecarboxamide (i.e. the title product of Step A) (100 mg) in dichloromethane (10 mL) was added MCPBA (47 mg, 70%) at −78° C. The reaction mixture was stirred at −78 to −70° C. for 2.5 h, then quenched with saturated sodium bicarbonate, extracted with dichloromethane, washed with brine, dried with sodium sulfate, and concentrated to afford the title compound as a white solid (102 mg, 99% yield).

Workup

customquenched with saturated sodium bicarbonate
extractionextracted with dichloromethane
washwashed with brine
dry with materialdried with sodium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-0fc1356b12bf456e9229c505b02365ef
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08623875B2

Reaction notes

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