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Ethyl bromopyruvate → 5-(4-Ethoxycarbonyl-thiazol-2-yl)-indole-1-carboxylic acid tert-butyl ester

HRID 460203
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HRID 460203 반응식
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17](=[S:19])[NH2:18])=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[CH2:21][C:22](=O)[C:23]([O:25][CH2:26][CH3:27])=[O:24]>CCO>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17]3[S:19][CH:21]=[C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[N:18]=3)=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]
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참가 물질

4

반응물 2

HCID 66144Ethyl bromopyruvateHCID 768465795-Thiocarbamoyl-indole-1-carboxylic acid tert-butyl ester

생성물 1

HCID 694116205-(4-Ethoxycarbonyl-thiazol-2-yl)-indole-1-carboxylic acid tert-butyl ester

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
60 °C

실험 절차

To a solution of 5-thiocarbamoyl-indole-1-carboxylic acid tert-butyl ester (13.16 g, 47.6 mmol) and 250 mL of EtOH was added ethyl bromopyruvate (6.05 mL, 48.2 mmol). The resulting solution was stirred at 60° C. for 1.5 h, then concentrated in vacuo. The resulting solid was purified by flash chromatography on silica gel using 5% EtOAc/hexane→80% EtOAc/hexane→CH2Cl2 as the eluant to give a white solid. MS m/z: 373 (M+1). Calc'd for C19H20N2O4S-372.44.

후처리

  1. concentrationconcentrated in vacuo
  2. customThe resulting solid was purified by flash chromatography on silica gel using 5% EtOAc/hexane→80% EtOAc/hexane→CH2Cl2 as the eluant
  3. customto give a white solid

출처 및 근거

ORD 기록
ord-d929670f0efe4441ae82901cb053581d
출처 데이터셋
uspto-grants-2007_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07196104B2

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