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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
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HRID 2388190 반응식
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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매

2
HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-de17dda57e82431caaff7c69ad99f9fb
출처 데이터셋
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08269008B2

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