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

HRID 248668

反応式

HRID 248668 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-2bcdfcdab4524984be5bd1e9b06e5e26
出典データセット
uspto-grants-1993_05
特許番号
US05210266

関連ノート

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