4-Methoxybutyric acid → HCID 178494907, 화합물

HRID 1176547

반응식

HRID 1176547 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

HCID 178494907HCID 178494907, 화합물

시약·촉매·용매 1

HCID 313Hydrochloric Acid용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-f2fbdfb1c30a4371a386cb4a87984fdb
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07842688B2

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