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

HRID 1072567
ノート
印刷プレビュー

反応式

HRID 1072567 の反応式
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]
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

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 30156371-Methoxyethanol溶媒

反応条件

温度
100 °C

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-32a9c4d335fe4975aa04f4a397029803
出典データセット
uspto-grants-2005_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06911465B1

反応ノート

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