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Ethyl Acetate → Ethyl 4-(((2,4-dimethoxybenzyl)(2-ethoxy-2-oxoethyl)amino)methyl)-3-(thiophen-2-yl)isoxazole-5-carboxylate

HRID 2388190
ノート
印刷プレビュー

反応式

HRID 2388190 の反応式
Br[CH2:2][C:3]1[C:4]([C:13]2[S:14][CH:15]=[CH:16][CH:17]=2)=[N:5][O:6][C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9].[CH2:18]([O:20][C:21](=[O:35])[CH2:22][NH:23][CH2:24][C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][C:26]=1[O:33][CH3:34])[CH3:19].C(=O)([O-])[O-].[K+].[K+].CCOC(C)=O>CN(C=O)C.O>[CH3:34][O:33][C:26]1[CH:27]=[C:28]([O:31][CH3:32])[CH:29]=[CH:30][C:25]=1[CH2:24][N:23]([CH2:2][C:3]1[C:4]([C:13]2[S:14][CH:15]=[CH:16][CH:17]=2)=[N:5][O:6][C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:22][C:21]([O:20][CH2:18][CH3:19])=[O:35]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 19895532Ethyl 2-(2,4-dimethoxybenzylamino)acetateHCID 67530400Ethyl 4-(bromomethyl)-3-(thiophen-2-yl)isoxazole-5-carboxylate

生成物 1

HCID 67530282Ethyl 4-(((2,4-dimethoxybenzyl)(2-ethoxy-2-oxoethyl)amino)methyl)-3-(thiophen-2-yl)isoxazole-5-carboxylate収率 27.3%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

Ethyl 4-(bromomethyl)-3-(thiophen-2-yl)isoxazole-5-carboxylate (16.5 mmol) was dissolved in 35 mL of DMF. N-(2,4-dimethoxybenzyl)glycine ethyl ester (4.2 g, 16.5 mmol) and potassium carbonate (4.5 g, 32.9 mmol) were added, and the mixture was stirred at room temperature for 16 h. EtOAc (100 mL) and water (100 mL) were added and the aqueous layer was extracted with additional EtOAc. The combined organic layer was washed with water and brine, and dried over MgSO4. After solvent was removed in vacuo, the crude was purified by flash chromatography (0-40% EtOAc/hexanes) to give 2.2 g of the title compound. MS: (+) m/z 489.44 (M+1).

後処理

  1. extractionthe aqueous layer was extracted with additional EtOAc
  2. washThe combined organic layer was washed with water and brine
  3. dry with materialdried over MgSO4
  4. customAfter solvent was removed in vacuo
  5. customthe crude was purified by flash chromatography (0-40% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-de17dda57e82431caaff7c69ad99f9fb
出典データセット
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08269008B2

反応ノート

読み込み中…

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