Triethylamine → (2R)-2-methanesulfonyloxy-2-((4S)-2-(3-acetoxy-2-methylphenyl)-4,5-dihydrooxazol-4-yl)ethanol

HRID 1016692노트

반응식

HRID 1016692 반응식
[CH3:1][S:2]([O:5][C@@H:6]1[C@@H:12]([NH:13][C:14](=[O:26])[C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][C:22](=[O:24])[CH3:23])[C:16]=2[CH3:25])[CH2:11]OC(C)(C)[O:8][CH2:7]1)(=[O:4])=[O:3].C(N(CC)CC)C>ClCCl>[CH3:1][S:2]([O:5][C@H:6]([C@@H:12]1[CH2:11][O:26][C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][C:22](=[O:24])[CH3:23])[C:16]=2[CH3:25])=[N:13]1)[CH2:7][OH:8])(=[O:3])=[O:4]

참가 물질

4

반응물 2

HCID 8471TriethylamineHCID 10787996(5R,6S)-N-(5-methanesulfonyloxy-2,2-dimethyl-1,3-dioxepan-6-yl)-3-acetoxy-2-methylbenzamide2회

생성물 1

HCID 10689674(2R)-2-methanesulfonyloxy-2-((4S)-2-(3-acetoxy-2-methylphenyl)-4,5-dihydrooxazol-4-yl)ethanol

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

(5R, 6S)-N-(5-Methanesulfonyloxy-2,2-dimethyl-1,3-dioxepan-6-yl)-3-acetoxy-2-methylbenzamide (compound [9], 34.2 g, 82.3 mmol) was dissolved in dichloromethane (340 ml) and boron trifluoride-diethyl ether complex (30.4 ml, 247 mmol) was added over 5 minutes with stirring at room temperature. The mixture was stirred for 40 hours at room temperature. Triethylamine (34.5 ml, 247 mmol) was added at not more than 15° C. and the solvent was distilled away under reduced pressure to ⅕ volume. The residue was diluted with ethyl acetate (340 ml) and washed successively with 10% brine (340 ml), 10% brine (340 ml) containing citric acid (17 g), and saturated brine (340 ml). After drying over magnesium sulfate, the solution was concentrated to 36 g to give a crude product of (2R)-2-methanesulfonyloxy-2-((4S)-2-(3-acetoxy-2-methylphenyl)-4,5-dihydrooxazol-4-yl)ethanol (compound [10]).

후처리

  1. additionboron trifluoride-diethyl ether complex (30.4 ml, 247 mmol) was added over 5 minutes
  2. stirringThe mixture was stirred for 40 hours at room temperature
  3. distillationthe solvent was distilled away under reduced pressure
  4. additionThe residue was diluted with ethyl acetate (340 ml)
  5. washwashed successively with 10% brine (340 ml), 10% brine (340 ml)
  6. additioncontaining citric acid (17 g), and saturated brine (340 ml)
  7. dry with materialAfter drying over magnesium sulfate
  8. concentrationthe solution was concentrated to 36 g

출처 및 근거

ORD 기록
ord-76886f857a034f11add315e9068e8795
출처 데이터셋
uspto-grants-2002_11
특허 번호
US06476232B2

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