Tetrabutylammonium Fluoride → Di-tert-butyl (1S,2S,5R,6S)-2-[(tert-butoxycarbonyl)amino]bicyclo[3.1.0]hex-3-ene-2,6-dicarboxylate

HRID 2172987노트

반응식

HRID 2172987 반응식
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[C:19]([O:23][C:24]([NH:26][C@@:27]1([C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])[CH2:32][C@H:31](OS(C)(=O)=O)[C@@H:30]2[C@H:28]1[C@H:29]2[C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])=[O:25])([CH3:22])([CH3:21])[CH3:20]>O1CCCC1.O>[C:19]([O:23][C:24]([NH:26][C@@:27]1([C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])[CH:32]=[CH:31][C@@H:30]2[C@H:28]1[C@H:29]2[C:38]([O:40][C:41]([CH3:43])([CH3:42])[CH3:44])=[O:39])=[O:25])([CH3:22])([CH3:20])[CH3:21]

참가 물질

5

반응물 2

HCID 2724141Tetrabutylammonium FluorideHCID 86695971HCID 86695971, 화합물

생성물 1

HCID 71681345Di-tert-butyl (1S,2S,5R,6S)-2-[(tert-butoxycarbonyl)amino]bicyclo[3.1.0]hex-3-ene-2,6-dicarboxylate수율 48%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

실험 절차

Add 1M tetrabutylammonium fluoride in tetrahydrofuran (3.84 mL, 3.84 mmol) to di-tert-butyl (1S,2S,4S,5R,6R)-2-[(tert-butoxycarbonyl)amino]-4-[(methylsulfonyl)oxy]bicyclo[3.1.0]hexane-2,6-dicarboxylate (600.00 mg, 1.22 mmol) in tetrahydrofuran (2.03 mL) and heat at reflux for 3 hours. The reaction is then cooled to room temperature, diluted with water, and extracted with ethyl acetate, washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure to give a residue. The residue is purified by flash chromatography eluting with 5-75% ethyl acetate in hexanes to give the title compound (0.23 g, 0.58 mmol, 48%).

후처리

  1. temperatureheat
  2. temperatureat reflux for 3 hours
  3. extractionextracted with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto give a residue
  9. customThe residue is purified by flash chromatography
  10. washeluting with 5-75% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-f31df39bb429447aaeab2ee101695153
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09056844B2

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