Tetrahydrofuran → Tert-butyl 4-(2-(ethylsulfonyl) quinazolin-7-yloxy)piperidine-1-carboxylate

HRID 2079669Notes

Reaction equation

C(S[C:4]1[N:13]=[CH:12][C:11]2[C:6](=[CH:7][C:8]([O:14][CH:15]3[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]3)=[CH:9][CH:10]=2)[N:5]=1)C.O[O:29][S:30]([O-:32])=O.[K+].[CH2:34]1COC[CH2:35]1>O>[CH2:34]([S:30]([C:4]1[N:13]=[CH:12][C:11]2[C:6](=[CH:7][C:8]([O:14][CH:15]3[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:26])([CH3:25])[CH3:27])=[O:22])[CH2:17][CH2:16]3)=[CH:9][CH:10]=2)[N:5]=1)(=[O:32])=[O:29])[CH3:35]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of tert-butyl 4-(2-(ethylthio) quinazolin-7-yloxy)piperidine-1-carboxylate (1 eq) in THF (5 ml) was added a solution of oxone in water (5 ml) at 0° C. The reaction mixture was stirred for 30 min at 0° C. then warmed to room temperature and stirred for 4 h. The reaction was quenched with satd. sodium thiosulfate solution and basified with 1N NaOH. The product was extracted from basic layer with DCM. The DCM extracts were combined together, washed with brine and dried over sodium sulfate. The purification by flash column chromatography (70% EtOAc/Hexane) provide pure product in 60% yield. ES/MS m/z 422.0 (MH+).

Workup

temperaturethen warmed to room temperature
stirringstirred for 4 h
customThe reaction was quenched with satd
extractionThe product was extracted from basic layer with DCM
washwashed with brine
dry with materialdried over sodium sulfate
customThe purification by flash column chromatography (70% EtOAc/Hexane)
customprovide pure product in 60% yield

Sources & evidence

ORD record: ord-a5c2aa3e3df84734893f40bc46cd8b66
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07932262B2

Reaction notes

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