Water → HCID 10134854, 화합물

HRID 1071856노트

반응식

HRID 1071856 반응식
[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

참가 물질

5

반응물 3

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 69744945HCID 69744945, 화합물

생성물 1

HCID 10134854HCID 10134854, 화합물

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c061686132b6473cb5626961bb61cb2f
출처 데이터셋
uspto-grants-2005_06
특허 번호
US06906206B2

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