m-Chloroperbenzoic acid → (S)-5-bromo-6-(1-tert-butoxy-2-(pivaloyloxy)ethyl)-2,7-dimethylquinoline 1-oxide

HRID 931751Notes

Reaction equation

[C:1]([O:7][CH2:8][C@H:9]([C:15]1[C:16]([Br:27])=[C:17]2[C:22](=[CH:23][C:24]=1[CH3:25])[N:21]=[C:20]([CH3:26])[CH:19]=[CH:18]2)[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].C1C=C(Cl)C=C(C(OO)=[O:36])C=1>C(Cl)(Cl)Cl>[Br:27][C:16]1[C:15]([C@H:9]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:8][O:7][C:1](=[O:6])[C:2]([CH3:5])([CH3:3])[CH3:4])=[C:24]([CH3:25])[CH:23]=[C:22]2[C:17]=1[CH:18]=[CH:19][C:20]([CH3:26])=[N+:21]2[O-:36]

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of (S)-2-(5-bromo-2,7-dimethylquinolin-6-yl)-2-tert-butoxyethyl pivalate (5E) (118 mg, 0.31 mmol) in chloroform (5 mL) was added mCPBA (209 mg, 77%, 0.93 mmol) 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 (52 mg, 37%). LCMS-ESI+ (m/z): 452.1, 454.1 (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-99a75cbcebb845e3984f3fe9febebb1c
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296758B2

Reaction notes

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