tert-Butanol → HCID 68429383, 화합물

HRID 889243노트

반응식

HRID 889243 반응식
Cl[S:2]([N:5]=[C:6]=[O:7])(=[O:4])=[O:3].[C:8]([OH:12])([CH3:11])([CH3:10])[CH3:9].[CH3:13][O:14][C:15](=[O:34])[CH2:16][NH:17][C:18]1[C:23]([F:24])=[CH:22][C:21]([Br:25])=[CH:20][C:19]=1[O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(N(CC)CC)C>C(Cl)Cl>[CH3:13][O:14][C:15](=[O:34])[CH2:16][N:17]([S:2](=[O:4])(=[O:3])[NH:5][C:6]([O:12][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:7])[C:18]1[C:23]([F:24])=[CH:22][C:21]([Br:25])=[CH:20][C:19]=1[O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

참가 물질

6

반응물 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 70918Chlorosulfonyl isocyanateHCID 68431677HCID 68431677, 화합물

생성물 1

HCID 68429383HCID 68429383, 화합물

시약·촉매·용매 1

HCID 6344Dichloromethane용매3회

실험 절차

To a solution of 1.25 g (8.83 mmol) of chlorosulfonyl isocyanate in 15 mL of methylene chloride is added dropwise a solution of 650 mg (8.83 mmol) of t-butanol in 5 mL methylene chloride. The solution is stirred at room temperature for 45 min. then a solution of 2.30 g (6.25 mmol) of (2-benzyloxy-4-bromo-6-fluorophenylamino)-acetic acid methyl ester and 1.25 g (12.4 mmol) of triethylamine in 10 mL methylene chloride is added dropwise. The mixture is stirred at room temperature for 3 h then is washed with water. The organic phase is dried over sodium sulfate and the solvent is removed under reduced pressure. The residual oil is purified by flash chromatography using 15% ethyl acetate/methylene chloride to elute the product as an oil: 1H NMR (CDCl3): δ 7.46-7.33 (m, 6H), 6.98 (d, J=9.1 Hz, 1H), 6.95 (s, 1H), 5.15 (s, 2H), 4.68 (d, J=18 Hz, 1H), 4.41 (d, J=18 Hz, 1H), 3.64 (s, 3H), 1.45 (s, 9H); MS (M−H)−=547.

후처리

  1. stirringThe mixture is stirred at room temperature for 3 h
  2. washthen is washed with water
  3. dry with materialThe organic phase is dried over sodium sulfate
  4. customthe solvent is removed under reduced pressure
  5. customThe residual oil is purified by flash chromatography
  6. washto elute the product as an oil

출처 및 근거

ORD 기록
ord-14534fef6fae4b96bae2d97f417aecfd
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08252820B2

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