Water → HCID 178427310, 화합물

HRID 1646041노트

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HRID 1646041 반응식
[C:1]1([CH3:17])[CH:6]=[CH:5][C:4]([S:7]([NH:10][C@@H:11]([CH2:14][CH2:15][OH:16])[CH2:12]O)(=[O:9])=[O:8])=[CH:3][CH:2]=1.C(N(CC)CC)C.[CH3:25][S:26](Cl)(=[O:28])=[O:27].O>C(Cl)Cl>[CH3:25][S:26]([O:16][CH2:15][CH2:14][CH:11]1[CH2:12][N@@:10]1[S:7]([C:4]1[CH:5]=[CH:6][C:1]([CH3:17])=[CH:2][CH:3]=1)(=[O:9])=[O:8])(=[O:28])=[O:27]

참가 물질

6

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 10934189(S)-2-(p-toluenesulfonylamino)-1,4-butanediol

생성물 1

HCID 178427310HCID 178427310, 화합물

시약·촉매·용매 1

HCID 6344Dichloromethane용매3회

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온도
-5 °C

실험 절차

(S)-2-(p-Toluenesulfonylamino)-1,4-butanediol, 2, (46 g) was dissolved in methylene chloride (450 mL) and triethylamine (60 g) was added. The resulting solution was cooled to -5° C. under a nitrogen atmosphere and a solution of methanesulfonyl chloride (42.0 g) in methylene chloride (110 mL) was added dropwise over 3 hours. The resulting mixture was stirred an additional 0.5 hour at 0° to 5° C. and water (150 mL) and methylene chloride (350 mL) were cautiously added. The layers were separated and the organic layer extracted with 0.1 N HCl (100 mL) and demineralized water (100 mL) and then concentrated under vacuum to give (S)-2-(2'-methanesulfonyloxy-ethyl)-1 (p-toluenesulfonyl)aziridine, 3, as a light yellow solid (57.2 g) which was used directly in the next step without further purification. A portion was recrystallized from ethyl acetate and hexanes: mp 78°-80° C.

후처리

  1. customThe layers were separated
  2. extractionthe organic layer extracted with 0.1 N HCl (100 mL) and demineralized water (100 mL)
  3. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-adf1d279c718480284428918397e81d7
출처 데이터셋
uspto-grants-1993_01
특허 번호
US05177217

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