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

HRID 2388168
ノート
印刷プレビュー

反応式

HRID 2388168 の反応式
Br[CH2:2][C:3]1[C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:5][O:6][C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9].[CH2:19]([O:21][C:22](=[O:36])[CH2:23][NH:24][CH2:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][C:27]=1[O:34][CH3:35])[CH3:20].C(=O)([O-])[O-].[K+].[K+].CCOC(C)=O>CN(C=O)C.O>[CH3:35][O:34][C:27]1[CH:28]=[C:29]([O:32][CH3:33])[CH:30]=[CH:31][C:26]=1[CH2:25][N:24]([CH2:2][C:3]1[C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:5][O:6][C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:23][C:22]([O:21][CH2:19][CH3:20])=[O:36]
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 67530071Ethyl 4-(bromomethyl)-3-phenylisoxazole-5-carboxylate

生成物 1

HCID 67530665Ethyl 4-(((2,4-dimethoxybenzyl)(2-ethoxy-2-oxoethyl)amino)methyl)-3-phenylisoxazole-5-carboxylate収率 67.7%

試薬・触媒・溶媒 2

HCID 962Water溶媒
HCID 6228Dimethylformamide溶媒

実験手順

Ethyl 4-(bromomethyl)-3-phenylisoxazole-5-carboxylate (28.1 g, 90.6 mmol) was dissolved in 200 mL of DMF. N-(2,4-dimethoxybenzyl)glycine ethyl ester (22.9 g, 90.6 mmol) and potassium carbonate (9.2 g, 66.4 mmol) were added, and the mixture was stirred at room temperature for 16 h. EtOAc (200 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 product was purified by flash chromatography (0-40% EtOAc/hexanes) to give 29.6 g of the title compound. MS: (+) m/z 483.73 (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 product was purified by flash chromatography (0-40% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-50f61de397cb4c8ebce1e57b86022f45
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

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