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

HRID 1689576노트

반응식

HRID 1689576 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 HPLC. 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 HPLC
  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-af9888e577624391be59c7d94f32cff9
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08153416B2

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