Water → HCID 10134854、化合物

HRID 1267870ノート

反応式

HRID 1267870 の反応式
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[OH:12][CH2:13][C@H:14]1[CH2:28][O:27][C:17]2[CH:18]=[CH:19][C:20]3[C:21](=[O:26])[CH:22]=[CH:23][O:24][C:25]=3[C:16]=2[O:15]1.O>N1C=CC=CC=1>[CH3:11][C:1]1[CH:6]=[CH:5][C:4]([S:7]([O:12][CH2:13][CH:14]2[CH2:28][O:27][C:17]3[CH:18]=[CH:19][C:20]4[C:21](=[O:26])[CH:22]=[CH:23][O:24][C:25]=4[C:16]=3[O:15]2)(=[O:9])=[O:8])=[CH:3][CH:2]=1

参加物

5

反応物 3

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 69744945HCID 69744945、化合物

生成物 1

HCID 10134854HCID 10134854、化合物

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

p-Toluenesulfonyl chloride (0.60 g, 3.15 mmole) was added to solution of (2S)-2-(hydroxymethyl)-2,3-dihydro-7H-[1,4]dioxino[2,3-h]chromen-7-one (0.41 g, 1.75 mmole) in 50 mL of pyridine. The solution was stirred at room temperature overnight under nitrogen. Water was added to quench the excess tosyl chloride and the solvent was removed in vacuum and replaced with methylene chloride. The solution was washed with 2N aqueous HCl, with saturated aqueous sodium bicarbonate, and with saturated brine, and dried over magnesium sulfate. Filtration, evaporation in vacuum and column chromatography on silica gel with 3% methanol/methylene chloride as eluant gave 0.36 g (54%) of the (R)-enantiomer of the title compound as a yellow solid, m.p. 190-191° C.

後処理

  1. customto quench the excess tosyl chloride
  2. customthe solvent was removed in vacuum
  3. washThe solution was washed with 2N aqueous HCl, with saturated aqueous sodium bicarbonate
  4. dry with materialwith saturated brine, and dried over magnesium sulfate
  5. filtrationFiltration, evaporation in vacuum and column chromatography on silica gel with 3% methanol/methylene chloride as eluant

出典と根拠

ORDレコード
ord-bbe7ffa924f24587b7b4a70421beaab1
出典データセット
uspto-grants-2003_04
特許番号
US06555560B2

反応ノート

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