p-Toluenesulfonic acid monohydrate → 1,3-Oxathiolane-2-methanol, 2-benzoate

HRID 1805943노트

반응식

HRID 1805943 반응식
[C:1]([O:9][CH2:10][C@@H:11]1[S:15][CH2:14][CH2:13][O:12]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[C:1]([O:9][CH2:10][CH:11]1[S:15][CH2:14][CH2:13][O:12]1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

4

반응물 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 596089912(S)-(benzoyloxymethyl)-1,3-oxathiolane

생성물 1

HCID 110640761,3-Oxathiolane-2-methanol, 2-benzoate수율 80%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

2(S)-(Benzoyloxymethyl)-1,3-oxathiolane (0.045 mmol, 10 mg, 1.0 equiv.), para-toluenesulfonic acid monohydrate (0.015 mmol, 3 mg, 0.3 equiv.) and toluene (1 mL) were heated to reflux and stirred while monitoring the racemization reaction by chiral HLPC. After 24 h, the reaction was allowed to cool to ambient temperature and washed with saturated sodium bicarbonate solution. The organic phase was dried over magnesium sulfate and concentrated by rotary evaporation to give 8 mg (80% yield) of (+/−)-2-(benzoyloxymethyl)-1,3-oxathiolane.

후처리

  1. temperatureto reflux
  2. customthe racemization reaction by chiral HLPC
  3. washwashed with saturated sodium bicarbonate solution
  4. dry with materialThe organic phase was dried over magnesium sulfate
  5. concentrationconcentrated by rotary evaporation

출처 및 근거

ORD 기록
ord-53ff4a43a6b74b6b8d0210107491c08e
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08354546B2

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