3-Amino-4-methylbenzoic acid → 3-[(2-Acetylthiomethyl-3-phenylpropionyl)amino]-4-methylbenzoic acid

HRID 248675

반응식

HRID 248675 반응식
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([OH:7])=[O:6].[C:12]([S:15][CH2:16][CH:17]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:18](Cl)=[O:19])(=[O:14])[CH3:13]>C(=O)([O-])O.[Na+].O.O1CCCC1>[C:12]([S:15][CH2:16][CH:17]([CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[C:18]([NH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([OH:7])=[O:6])=[O:19])(=[O:14])[CH3:13]

참가 물질

6

반응물 2

HCID 755683-Amino-4-methylbenzoic acidHCID 103777342-Acetylthiomethyl-3-phenyl-propionyl chloride

생성물 1

HCID 156701693-[(2-Acetylthiomethyl-3-phenylpropionyl)amino]-4-methylbenzoic acid수율 52.4%

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 516892Sodium Bicarbonate용매

실험 절차

3-Amino-4-methylbenzoic acid (1.5 g) is dissolved in a solution of sodium hydrogen carbonate (1.68 g) in water (25 ml), and to the mixture is added dropwise a solution of 2-acetylthiomethyl-3-phenylpropionyl chloride (2.86 g) in tetrahydrofuran (8 ml) with vigorously stirring, and the mixture is stirred at room temperature for 3 hours. Tetrahydrofuran is distilled off at a low temperature under reduced pressure, and the residue is washed with diethyl ether and acidified with hydrochloric acid, and the resulting oily substance is extracted with ethyl acetate. The extract is washed with saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate, and then the solvent is distilled off under reduced pressure. The oily residue is purified by a medium pressure column chromatography with CHP-20P (eluant, water-acetonitrile). The fractions containing the desired compound are collected, and acetonitrile is distilled off under reduced pressure, and the precipitated crystals are separated by filtration to give the title compound (1.93 g).

후처리

  1. stirringthe mixture is stirred at room temperature for 3 hours
  2. distillationTetrahydrofuran is distilled off at a low temperature under reduced pressure
  3. washthe residue is washed with diethyl ether
  4. extractionthe resulting oily substance is extracted with ethyl acetate
  5. washThe extract is washed with saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationthe solvent is distilled off under reduced pressure
  8. customThe oily residue is purified by a medium pressure column chromatography with CHP-20P (eluant, water-acetonitrile)
  9. additionThe fractions containing the desired compound
  10. customare collected
  11. distillationacetonitrile is distilled off under reduced pressure
  12. customthe precipitated crystals are separated by filtration

출처 및 근거

ORD 기록
ord-45fd81e8e1ef4735a88d03c53e885b71
출처 데이터셋
uspto-grants-1993_05
특허 번호
US05210266

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