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Triethylamine → ethyl 4-[(N-(methoxycarbonylmethyl)glycyl)amino]-N-(3,4-dichlorobenzyl)indole-2-carboxylate

HRID 1072567
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HRID 1072567 반응식
Cl[CH2:2][C:3]([NH:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[CH:8]=[C:9]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[N:10]2[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([Cl:23])[CH:17]=1)=[O:4].Cl.[CH3:30][O:31][C:32](=[O:35])[CH2:33][NH2:34].C(N(CC)CC)C>COC(O)C>[CH3:30][O:31][C:32]([CH2:33][NH:34][CH2:2][C:3]([NH:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[CH:8]=[C:9]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[N:10]2[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([Cl:23])[CH:17]=1)=[O:4])=[O:35]
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참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 122755Glycine methyl ester hydrochlorideHCID 22387275Ethyl 4-chloroacetamido-N-(3,4-dichlorobenzyl)indole-2-carboxylate

생성물 1

HCID 22387276ethyl 4-[(N-(methoxycarbonylmethyl)glycyl)amino]-N-(3,4-dichlorobenzyl)indole-2-carboxylate

시약·촉매·용매 1

HCID 30156371-Methoxyethanol용매

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온도
100 °C

실험 절차

Ethyl 4-chloroacetamido-N-(3,4-dichlorobenzyl)indole-2-carboxylate (0.4 g), glycine methyl ester hydrochloride (0.57 g) and triethylamine (1.25 ml) were dissolved in methoxyethanol (4.0 ml) and the reaction heated at 100° C. for 6 hours. The reaction was cooled and partitioned between water and ethyl acetate. Combined organic extracts were dried (MgSO4) and concentrated and the residue purified by chromatography using toluene:ethyl acetate (1:1) as eluent to give the product, ethyl 4-[(N-(methoxycarbonylmethyl)glycyl)amino]-N-(3,4-dichlorobenzyl)indole-2-carboxylate, as a pale yellow solid (0.17 g, 38%); NMR d (CD3SOCD3) 1.28 (t, 3H), 3.44 (s, 2H), 3.50 (s, 2H), 3.63 (s, 3H), 4.28 (q, 2H), 5.82 (s, 2H), 6.88 (dd, 1H), 7.10-7.30 (m, 4H), 7.50 (d, 1H), 7.69 (s, 1H), 7.80 (dd, 1H), 10.00 (brs, 1H); M/z (+) 494, 492 (M+).

후처리

  1. temperatureThe reaction was cooled
  2. custompartitioned between water and ethyl acetate
  3. dry with materialCombined organic extracts were dried (MgSO4)
  4. concentrationconcentrated
  5. customthe residue purified by chromatography

출처 및 근거

ORD 기록
ord-32a9c4d335fe4975aa04f4a397029803
출처 데이터셋
uspto-grants-2005_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06911465B1

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