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

HRID 1620887ノート

反応式

HRID 1620887 の反応式
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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9144d066b07b4c629f868cbaba1f3e71
出典データセット
uspto-grants-2014_07
特許番号
US08772502B2

反応ノート

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