m-Chloroperbenzoic acid → (S)-6-(1-tert-butoxy-2-ethoxy-2-oxoethyl)-5-(4-chlorophenyl)-2,7-dimethylquinoline 1-oxide

HRID 931765Notes

Reaction equation

[C:1]([O:5][C@@H:6]([C:12]1[C:13]([C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=2)=[C:14]2[C:19](=[CH:20][C:21]=1[CH3:22])[N:18]=[C:17]([CH3:23])[CH:16]=[CH:15]2)[C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH3:4])([CH3:3])[CH3:2].C1C=C(Cl)C=C(C(OO)=[O:39])C=1>ClCCl>[C:1]([O:5][C@@H:6]([C:12]1[C:13]([C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=2)=[C:14]2[C:19](=[CH:20][C:21]=1[CH3:22])[N+:18]([O-:39])=[C:17]([CH3:23])[CH:16]=[CH:15]2)[C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH3:2])([CH3:3])[CH3:4]

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of (S)-ethyl 2-tert-butoxy-2-(5-(4-chlorophenyl)-2,7-dimethylquinolin-6-yl)acetate (100 mg, 0.25 mmol) in dichloromethane (5 mL) was added a solution of mCPBA (114 mg, 77%, 0.51 mmol) in DCM (2 mL) at 0° C. The mixture was stirred at 0° C. for 1 hour before quenched with NaHCO3 solution. The mixture was extracted with DCM (30 mL), washed with NaHCO3 solution, water and brine, dried over Na2SO4, filtered and concentrated in vacuo. The obtained residue was purified by flash chromatography to provide the desired product (104 mg, 94%). LCMS-ESI+ (m/z): 442.2, 444.3 (M+H)+.

Workup

custombefore quenched with NaHCO3 solution
extractionThe mixture was extracted with DCM (30 mL)
washwashed with NaHCO3 solution, water and brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe obtained residue was purified by flash chromatography

Sources & evidence

ORD record: ord-7223c1da5f5342b69b2df1eefbbb8478
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296758B2

Reaction notes

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