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Dimethyl Disulfide → ethyl 4-[7-bromo-1-[2-(ethyloxy)-2-oxoethyl]-2-(methylthio)-1H-indol-3-yl]butanoate

HRID 12617
ノート
印刷プレビュー

反応式

HRID 12617 の反応式
CS[S:3][CH3:4].S(Cl)(Cl)(=O)=O.[Br:10][C:11]1[CH:12]=[CH:13][CH:14]=[C:15]2[C:19]=1[N:18]([CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH:17]=[C:16]2[CH2:26][CH2:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30].C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[Br:10][C:11]1[CH:12]=[CH:13][CH:14]=[C:15]2[C:19]=1[N:18]([CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:17]([S:3][CH3:4])=[C:16]2[CH2:26][CH2:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 12232Dimethyl DisulfideHCID 24648Sulfuryl chlorideHCID 516892Sodium BicarbonateHCID 66738782ethyl 4-{7-bromo-1-[2-(ethyloxy)-2-oxoethyl]-1H-indol-3-yl}butanoate

生成物 1

HCID 68693460ethyl 4-[7-bromo-1-[2-(ethyloxy)-2-oxoethyl]-2-(methylthio)-1H-indol-3-yl]butanoate

試薬・触媒・溶媒 1

HCID 6212
Chloroform
溶媒
2 回

反応条件

温度
-5 °C

実験手順

To a chloroform (0.8 mL) solution of dimethyl disulfide (30 mg), sulfuryl chloride (34 mg) was added at −15° C. and the mixture was stirred at −5° C. for 1.5 hours. To the reaction mixture, a chloroform (0.5 mL) solution of the compound prepared in Example 43, namely, ethyl 4-{7-bromo-1-[2-(ethyloxy)-2-oxoethyl]-1H-indol-3-yl}butanoate (100 mg) was added at −78° C., followed by stirring at room temperature for 3 hours. To the reaction mixture, an aqueous saturated sodium hydrogen carbonate solution was added under ice cooling, followed by extraction with ethyl acetate. The organic layer was washed in turn with an aqueous saturated sodium hydrogen carbonate solution, water and saturated saline, dried over anhydrous magnesium sulfate and then concentrated. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=95:5→91:9) to obtain the titled compound having the following physical properties (70 mg).

後処理

  1. stirringby stirring at room temperature for 3 hours
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed in turn with an aqueous saturated sodium hydrogen carbonate solution, water and saturated saline
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=95:5→91:9)

出典と根拠

ORDレコード
ord-89b9fac623f644f58e5b221f3871bc84
出典データセット
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07728023B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート