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

HRID 2079669
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HRID 2079669 반응식
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]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 8028TetrahydrofuranHCID 23707502Potassium hydroxy sulfiteHCID 67101955Tert-butyl 4-(2-(ethylthio)quinazolin-7-yloxy)piperidine-1-carboxylate

생성물 1

HCID 67102269Tert-butyl 4-(2-(ethylsulfonyl) quinazolin-7-yloxy)piperidine-1-carboxylate수율 60%

시약·촉매·용매 1

HCID 962Water용매

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온도
0 °C

실험 절차

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+).

후처리

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

출처 및 근거

ORD 기록
ord-a5c2aa3e3df84734893f40bc46cd8b66
출처 데이터셋
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07932262B2

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