Triethylamine → 3-[(2-Acetylthiomethyl-3-phenylpropionyl)amino]-5-methylbenzoic acid

HRID 248668

반응식

HRID 248668 반응식
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([CH3:11])[CH:10]=1)[C:5]([OH:7])=[O:6].C(N(CC)CC)C.[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]([CH3:11])[CH:10]=1)[C:5]([OH:7])=[O:6])=[O:26])(=[O:21])[CH3:20]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 103777342-Acetylthiomethyl-3-phenyl-propionyl chlorideHCID 184056783-Amino-5-methylbenzoic acid

생성물 1

HCID 156701493-[(2-Acetylthiomethyl-3-phenylpropionyl)amino]-5-methylbenzoic acid수율 51.8%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

3-Amino-5-methylbenzoic acid (1.9 g) is dissolved in a 60% aqueous solution of tetrahydrofuran (30 ml) containing triethylamine (2.3 g), and to the mixture is added dropwise a solution of 2-acetylthiomethyl-3-phenyl-propionyl chloride (3.2 g) in tetrahydrofuran (20 ml) with stirring under ice cooling, and the mixture is stirred at room temperature for 2 hours. 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 acetonitrile and purified by a medium pressure column chromatography with CHP-20P (eluant, water-acetonitrile). The fractions containing the desired compound are collected and concentrated into dryness under reduced pressure to give the title compound (2.4 g).

후처리

  1. stirringthe mixture is stirred at room temperature for 2 hours
  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 acetonitrile
  8. custompurified by a medium pressure column chromatography with CHP-20P (eluant, water-acetonitrile)
  9. additionThe fractions containing the desired compound
  10. customare collected
  11. concentrationconcentrated into dryness under reduced pressure

출처 및 근거

ORD 기록
ord-2bcdfcdab4524984be5bd1e9b06e5e26
출처 데이터셋
uspto-grants-1993_05
특허 번호
US05210266

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