4-Methoxybutyric acid → HCID 178494907、化合物

HRID 1712541

反応式

HRID 1712541 の反応式
[NH2:1][C:2]1[C:11]([NH2:12])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[CH3:13][O:14][CH2:15][CH2:16][CH2:17][C:18](O)=O>Cl>[CH3:13][O:14][CH2:15][CH2:16][CH2:17][C:18]1[NH:1][C:2]2[C:3]([C:4]([O:6][CH3:7])=[O:5])=[CH:8][CH:9]=[CH:10][C:11]=2[N:12]=1

参加物

4

反応物 2

HCID 922644-Methoxybutyric acidHCID 5718252,3-Diaminobenzoic acid methyl ester

生成物 1

HCID 178494907HCID 178494907、化合物

試薬・触媒・溶媒 1

HCID 313Hydrochloric Acid溶媒

実験手順

A solution of 4 g of methyl 2,3-diaminobenzoate and 8.53 g of 4-methoxybutyric acid in 70 ml of 4N HCl is stirred at reflux over 21 hours. The reaction mixture is cooled to room temperature and partitioned between ethyl acetate and water. The aqueous phase is concentrated by evaporation—the residue is diluted with 100 ml of methanol and 2 ml of conc. H2SO4 and stirred at reflux over 45 hours. The reaction mixture is cooled to room temperature, neutralized with saturated aqueous sodium bicarbonate solution and concentrated by evaporation. The residue is diluted with water and extracted with ethyl acetate (2×)—the combined organic phases are dried over sodium sulphate and concentrated by evaporation. The title compound is obtained as a red solid from the residue by means of flash chromatography (SiO2 60F). Rf=0.31 (95:5 dichloromethane-methanol); Rt=2.53.

後処理

  1. temperatureat reflux over 21 hours
  2. custompartitioned between ethyl acetate and water
  3. concentrationThe aqueous phase is concentrated by evaporation—the residue
  4. additionis diluted with 100 ml of methanol and 2 ml of conc. H2SO4
  5. temperatureat reflux over 45 hours
  6. temperatureThe reaction mixture is cooled to room temperature
  7. concentrationconcentrated by evaporation
  8. additionThe residue is diluted with water
  9. extractionextracted with ethyl acetate (2×)—the combined organic phases
  10. dry with materialare dried over sodium sulphate
  11. concentrationconcentrated by evaporation

出典と根拠

ORDレコード
ord-81f74e0aef19449db13778ea783e8629
出典データセット
uspto-grants-2010_09
特許番号
US07790715B2

関連ノート

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