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

HRID 2388197Notes

Reaction equation

HRID 2388197 reaction equation
Br[CH2:2][C:3]1[C:4]([C:13]2[CH:18]=[CH:17][N: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][N: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]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 19895532Ethyl 2-(2,4-dimethoxybenzylamino)acetateHCID 67531296Ethyl 4-(bromomethyl)-3-(pyridin-4-yl)isoxazole-5-carboxylate

Product 1

HCID 67530058Ethyl 4-(((2,4-dimethoxybenzyl)(2-ethoxy-2-oxoethyl)amino)methyl)-3-(pyridin-4-yl)isoxazole-5-carboxylateYield 21%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Ethyl 4-(bromomethyl)-3-(pyridin-4-yl)isoxazole-5-carboxylate (1.5 g, 4.82 mmol) was dissolved in 20 mL of DMF. N-(2,4-dimethoxybenzyl)glycine ethyl ester (1.22 g, 4.82 mmol) and potassium carbonate (1.33 g, 9.65 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 (0-50% EtOAc/hexanes) to give 0.49 g of the title compound. MS: (+) m/z 484.48 (M+1).

Workup

  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 (0-50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-67d97979f22944f1af7a5864c6d99e42
Source dataset
uspto-grants-2012_09
Patent number
US08269008B2

Reaction notes

Loading…