m-Chloroperbenzoic acid → 3-{[5-(Methylsulfinyl)-1,3-thiazol-2-yl]carbamoyl}phenyl acetate

HRID 1620887

반응식

HRID 1620887 반응식
ClC1C=CC=C(C(OO)=[O:9])C=1.[C:12]([O:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([C:22](=[O:31])[NH:23][C:24]2[S:25][C:26]([S:29][CH3:30])=[CH:27][N:28]=2)[CH:17]=1)(=[O:14])[CH3:13]>ClCCl>[C:12]([O:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([C:22](=[O:31])[NH:23][C:24]2[S:25][C:26]([S:29]([CH3:30])=[O:9])=[CH:27][N:28]=2)[CH:17]=1)(=[O:14])[CH3:13]

참가 물질

4

반응물 2

HCID 70297m-Chloroperbenzoic acidHCID 575718763-{[5-(Methylsulfanyl)-1,3-thiazol-2-yl]carbamoyl}phenyl acetate

생성물 1

HCID 569693943-{[5-(Methylsulfinyl)-1,3-thiazol-2-yl]carbamoyl}phenyl acetate수율 106.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

A solution of m-chloroperbenzoic acid (0.458 g, 2.04 mmol, maximum 77%) is dissolved in dichloromethane (8.0 mL) and added dropwise over 15 minutes to a solution of 516 (0.630 g, 2.04 mmol) dissolved in dichloromethane (25.0 mL). The reaction is stirred at room temperature for 6 hours. The reaction is then partitioned between dichloromethane and saturated aqueous sodium thiosulfate. The organic layer is washed again with a saturated aqueous sodium thiosulfate, twice with saturated aqueous sodium bicarbonate and once with brine. The dichloromethane layer is dried over magnesium sulfate and concentrated in vacuo to give crude 8 (0.704 g, >100%), which is contaminated with traces of residual 3-chlorobenzoic acid. The crude product is re-dissolved in ethyl acetate and washed three times with a saturated aq. sodium bicarbonate, dried using magnesium sulfate and concentrated in vacuo to give a tan solid. The residue is dissolved in THF, and the light brown solution was filtered through a plug of Magnesol. The filter pad is washed well with THF, and the colorless filtrate is concentrated in vacuo to give 8 as a white solid.

후처리

  1. customThe reaction is then partitioned between dichloromethane and saturated aqueous sodium thiosulfate
  2. washThe organic layer is washed again with a saturated aqueous sodium thiosulfate, twice with saturated aqueous sodium bicarbonate and once with brine
  3. dry with materialThe dichloromethane layer is dried over magnesium sulfate
  4. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-9144d066b07b4c629f868cbaba1f3e71
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08772502B2

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