tert-Butanol → HCID 86615516, 화합물

HRID 2045775노트

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HRID 2045775 반응식
[C:1]([O:5][C:6](=[O:24])[NH:7][C@H:8]1CC(=C)C[O:10][C@@H:9]1[C:15]1[CH:20]=[C:19]([F:21])[C:18]([F:22])=[CH:17][C:16]=1[F:23])([CH3:4])([CH3:3])[CH3:2].C[N+]1([O-])CC[O:29]CC1.S(=O)(O)[O-].[Na+].C(OCC)(=O)C.[C:44]([OH:48])([CH3:47])([CH3:46])[CH3:45]>CC(C)=O.O.[Os](=O)(=O)(=O)=O>[OH:48][C:44]1([CH2:47][OH:29])[CH2:46][O:10][C@H:9]([C:15]2[CH:20]=[C:19]([F:21])[C:18]([F:22])=[CH:17][C:16]=2[F:23])[C@@H:8]([NH:7][C:6](=[O:24])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:45]1

참가 물질

9

반응물 5

HCID 6386tert-ButanolHCID 8857Ethyl AcetateHCID 82029Methyl morpholine oxideHCID 23665763Sodium BisulfiteHCID 86615515HCID 86615515, 화합물

생성물 1

HCID 86615516HCID 86615516, 화합물

시약·촉매·용매 3

HCID 30318Osmium Tetroxide촉매HCID 180Acetone용매HCID 962Water용매

실험 절차

To a solution of tert-butyl[(2R,3S)-5-methylene-2-(2,4,5-trifluorophenyl)tetrahydro-2H-pyran-3-yl]carbamate (203 mg, 0.59 mmol) in tert-butyl alcohol (6 mL), acetone (3 mL) and water (1.5 mL) was added osmium tetroxide (0.113 mL of 2.5% solution in tert-butyl alcohol, 0.009 mmol). The resultant mixture was stirred at room temperature for 10 minutes and then treated with N-methylmorpholine N-oxide (92 mg, 0.79 mmol) and stirred. After two days, the reaction mixture was treated with aqueous sodium bisulfite solution (5 mL, 2.0/V) followed after 10 min by ethyl acetate. The organic layer was washed successively with 2N hydrochloric acid and saturated aqueous sodium bicarbonate solution, dried over anhydrous sodium sulfate, filtered and evaporated to yield tert-butyl [(2R,3S)-5-hydroxy-5-(hydroxymethyl)-2-(2,4,5-trifluorophenyl)tetrahydro-2H-pyran-3-yl]carbamate which was used in the next step without further purification.

후처리

  1. washThe organic layer was washed successively with 2N hydrochloric acid and saturated aqueous sodium bicarbonate solution
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. customevaporated

출처 및 근거

ORD 기록
ord-6880a00cc1944e42a701dca4792c8a5c
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08592371B2

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