Sodium Carbonate → 3-[(2-Acetylthiomethyl-3-phenylpropionyl)amino]-5-ethylbenzoic acid

HRID 1646297

반응식

HRID 1646297 반응식
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([CH2:11][CH3:12])[CH:10]=1)[C:5]([OH:7])=[O:6].C(=O)([O-])[O-].[Na+].[Na+].[C:19]([S:22][CH2:23][CH:24]([CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:25](Cl)=[O:26])(=[O:21])[CH3:20]>O1CCCC1>[C:19]([S:22][CH2:23][CH:24]([CH2:28][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[C:25]([NH:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([CH2:11][CH3:12])[CH:10]=1)[C:5]([OH:7])=[O:6])=[O:26])(=[O:21])[CH3:20]

참가 물질

5

반응물 3

HCID 10340Sodium CarbonateHCID 103777342-Acetylthiomethyl-3-phenyl-propionyl chlorideHCID 197639303-Amino-5-ethylbenzoic acid

생성물 1

HCID 156702113-[(2-Acetylthiomethyl-3-phenylpropionyl)amino]-5-ethylbenzoic acid수율 62.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

3-Amino-5-ethylbenzoic acid (2.1 g) is dissolved in a 33% aqueous solution of tetrahydrofuran (30 ml) containing sodium carbonate (1.3 g), and to the mixture is added dropwise a solution of 2-acetylthiomethyl-3-phenylpropionyl chloride (3.0 g) in tetrahydrofuran (20 ml) with stirring under ice cooling, and the mixture is stirred at room temperature for one hour. Tetrahydrofuran is distilled off under reduced pressure, and the residue is extracted with ethyl acetate (100 ml). The extract is washed with saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate, and then ethyl acetate is distilled off under reduced pressure. The residue is dissolved in methanol and purified by a medium pressure column chromatography with CHP-20P (eluant, water-methanol). The fractions containing the desired compound are collected and concentrated into dryness under reduced pressure to give the title compound (2.8 g).

후처리

  1. stirringthe mixture is stirred at room temperature for one hour
  2. distillationTetrahydrofuran is distilled off under reduced pressure
  3. extractionthe residue is extracted with ethyl acetate (100 ml)
  4. washThe extract is washed with saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationethyl acetate is distilled off under reduced pressure
  7. dissolutionThe residue is dissolved in methanol
  8. custompurified by a medium pressure column chromatography with CHP-20P (eluant, water-methanol)
  9. additionThe fractions containing the desired compound
  10. customare collected
  11. concentrationconcentrated into dryness under reduced pressure

출처 및 근거

ORD 기록
ord-8719bd8ace2e40629c0f009bda920e06
출처 데이터셋
uspto-grants-1993_01
특허 번호
US05179125

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