Tetrabutylammonium Fluoride → tert-butyl N-(4-[[(12R)-12-(2-hydroxyethyl)-8-thia-4,6-diazatricyclo[7.4.0.0[2,7]]trideca-1(9),2(7),3,5-tetraen-3-yl]oxy]cyclohexyl)carbamate

HRID 1504022노트

반응식

HRID 1504022 반응식
[Si]([O:8][CH2:9][CH2:10][C@H:11]1[CH2:23][C:22]2[C:21]3[C:20]([O:24][CH:25]4[CH2:30][CH2:29][CH:28]([NH:31][C:32](=[O:38])[O:33][C:34]([CH3:37])([CH3:36])[CH3:35])[CH2:27][CH2:26]4)=[N:19][CH:18]=[N:17][C:16]=3[S:15][C:14]=2[CH2:13][CH2:12]1)(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[OH:8][CH2:9][CH2:10][C@H:11]1[CH2:23][C:22]2[C:21]3[C:20]([O:24][CH:25]4[CH2:26][CH2:27][CH:28]([NH:31][C:32](=[O:38])[O:33][C:34]([CH3:36])([CH3:35])[CH3:37])[CH2:29][CH2:30]4)=[N:19][CH:18]=[N:17][C:16]=3[S:15][C:14]=2[CH2:13][CH2:12]1

참가 물질

4

반응물 2

HCID 2724141Tetrabutylammonium FluorideHCID 86695178HCID 86695178, 화합물

생성물 1

HCID 86695177tert-butyl N-(4-[[(12R)-12-(2-hydroxyethyl)-8-thia-4,6-diazatricyclo[7.4.0.0[2,7]]trideca-1(9),2(7),3,5-tetraen-3-yl]oxy]cyclohexyl)carbamate수율 81%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of tert-butyl N-(4-[[(12R)-12-[2-[(tert-butyldimethylsilyl)oxy]ethyl]-8-thia-4,6-diazatricyclo[7.4.0.0[2,7]]trideca-1(9),2 (7),3,5-tetraen-3-yl]oxy]cyclohexyl)carbamate (200 mg, 0.36 mmol, 1.00 equiv) in 6 mL of THF was added TBAF (186 mg, 0.71 mmol, 2.00 equiv) at room temperature and the resulting solution was stirred overnight at ambient temperature. The reaction was then quenched with water, extracted with 3×30 mL of ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and concentrated under vacuum. Purification by column chromatography on silica gel with ethyl acetate/petroleum ether (1:2) afford 129 mg (81%) of the desired tert-butyl N-(4-[[(12R)-12-(2-hydroxyethyl)-8-thia-4,6-diazatricyclo[7.4.0.0[2,7]]trideca-1(9),2(7),3,5-tetraen-3-yl]oxy]cyclohexyl)carbamate as a yellow oil.

후처리

  1. customThe reaction was then quenched with water
  2. extractionextracted with 3×30 mL of ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under vacuum
  6. customPurification by column chromatography on silica gel with ethyl acetate/petroleum ether (1:2)

출처 및 근거

ORD 기록
ord-76674180dfad4917a991d26d03eff6fd
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09212190B2

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