Ethyl Acetate → [4-(4-Dimethylsulfamoyl-benzoyl)-naphthalen-2-yl]-acetic acid ethyl ester

HRID 1644716

반응식

HRID 1644716 반응식
C(O[C:4](=O)[CH2:5][CH2:6]C=O)C.C([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]#[C:19][C:20]1[CH:25]=[CH:24][C:23]([S:26]([N:29]([CH3:31])[CH3:30])(=[O:28])=[O:27])=[CH:22][CH:21]=1)=O.[C:32]([O:35][CH2:36][CH3:37])(=[O:34])[CH3:33].[O:38]1CCOCC1>[Au](Br)(Br)Br>[CH2:36]([O:35][C:32](=[O:34])[CH2:33][C:5]1[CH:6]=[C:18]([C:19](=[O:38])[C:20]2[CH:25]=[CH:24][C:23]([S:26](=[O:27])(=[O:28])[N:29]([CH3:30])[CH3:31])=[CH:22][CH:21]=2)[C:13]2[C:12](=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:4]=1)[CH3:37]

참가 물질

6

반응물 4

HCID 8857Ethyl AcetateHCID 312751,4-DioxaneHCID 82395Ethyl 4-oxobutanoateHCID 593508554-(2-formyl-phenylethynyl)-N,N-dimethyl-benzenesulfonamide

생성물 1

HCID 59350849[4-(4-Dimethylsulfamoyl-benzoyl)-naphthalen-2-yl]-acetic acid ethyl ester수율 29%

시약·촉매·용매 1

HCID 82525Gold tribromide촉매

반응 조건

온도
100 °C

실험 절차

A suspension of gold(III) bromide (38 mg, 0.087 mmol), 4-oxo-butyric acid ethyl ester (377 mg, 2.9 mmol) and 4-(2-formyl-phenylethynyl)-N,N-dimethyl-benzenesulfonamide (454 mg, 1.45 mmol) in anhydrous dioxane (10 mL) was heated at 100° C. for 4 hours. After being cooled to room temperature, the mixture was treated with ethyl acetate, and then washed with water. The collected organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (RediSep® Flash column, 230-400 mesh, 25-60% ethyl acetate in hexane) gave [4-(4-dimethylsulfamoyl-benzoyl)-naphthalen-2-yl]-acetic acid ethyl ester (180 mg, 29%). MS (ESI+) cald. for C23H23NO5S [(M+H)+] 425, obsd. 426.

후처리

  1. temperatureAfter being cooled to room temperature
  2. washwashed with water
  3. dry with materialThe collected organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-5b350a69c57e4ada870ac98732ece1a2
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08124629B2

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