Water → HCID 178427310、化合物

HRID 1655635ノート

反応式

HRID 1655635 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

HCID 178427310HCID 178427310、化合物

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒3 回

反応条件

温度
-5 °C

実験手順

(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 0.1N HCl (100 mL) and demineralized water (100 mL) and then concentrated under vacuum to give (S)-2-(2'-methanesulfonyloxyethyl)-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.

後処理

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

出典と根拠

ORDレコード
ord-b57210fb63c846e28ccdc4a3b3a32369
出典データセット
uspto-grants-1993_10
特許番号
US05250704

反応ノート

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