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Methyl bromoacetate → [[3-(Aminooxoacetyl)-2-ethyl-1-(phenylmethyl)-1H-indol-4-yl]amino]acetic acid methyl ester

HRID 3388
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HRID 3388 반응식
Br[CH2:2][C:3]([O:5][CH3:6])=[O:4].[NH2:7][C:8]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:9]=1[C:10]([C:26](=[O:30])[C:27]([NH2:29])=[O:28])=[C:11]([CH2:24][CH3:25])[N:12]2[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CN(C=O)C.O>[CH3:6][O:5][C:3](=[O:4])[CH2:2][NH:7][C:8]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:9]=1[C:10]([C:26](=[O:30])[C:27]([NH2:29])=[O:28])=[C:11]([CH2:24][CH3:25])[N:12]2[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1
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참가 물질

5

반응물 2

HCID 60984Methyl bromoacetateHCID 107581224-Amino-2-Ethyl-alpha-oxo-1-(phenylmethyl)-1H-indole-3-Acetamide

생성물 1

HCID 10691962[[3-(Aminooxoacetyl)-2-ethyl-1-(phenylmethyl)-1H-indol-4-yl]amino]acetic acid methyl ester수율 64%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

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온도
60 °C

실험 절차

Methyl bromoacetate (0.07 ml, 0.78 mmol) was added to 250 mg (0.78 mmol) of 4-Amino-2-Ethyl-α-oxo-1-(phenylmethyl)-1H-indole-3-Acetamide in 4 ml of DMF, stirred at 60° C. for 0.5 hour, and then at room temperature for 20 hours. The mixture was diluted with water and extracted with EtOAc. The EtOAC solution was washed with brine, dried over MgSO4, and evaporated in vacuo. The residue was chromatographed over silica gel eluting with Hexane/50 to 100% EtOAc to give 196 mg (64%) of [[3-(Aminooxoacetyl)-2-ethyl-1-(phenylmethyl)-1H-indol-4-yl]amino]acetic acid methyl ester melting at 188°-193° C.

후처리

  1. waitat room temperature for 20 hours
  2. extractionextracted with EtOAc
  3. washThe EtOAC solution was washed with brine
  4. dry with materialdried over MgSO4
  5. customevaporated in vacuo
  6. customThe residue was chromatographed over silica gel eluting with Hexane/50 to 100% EtOAc

출처 및 근거

ORD 기록
ord-e62040325e0347dba1d20052ff7e6f97
출처 데이터셋
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05733923

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