Hydrochloric Acid → Ethyl 3-[(2-mercaptomethyl-3-phenylpropionyl)amino]benzoate

HRID 248704ノート

反応式

HRID 248704 の反応式
C([S:4][CH2:5][CH:6]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:7]([NH:9][C:10]1[CH:11]=[C:12]([CH:18]=[CH:19][CH:20]=1)[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:8])(=O)C.N1CCCC1.Cl>C(#N)C>[SH:4][CH2:5][CH:6]([CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[C:7]([NH:9][C:10]1[CH:11]=[C:12]([CH:18]=[CH:19][CH:20]=1)[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:8]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 31268PyrrolidineHCID 15670143Ethyl 3-[(2-acetylthiomethyl-3-phenylpropionyl)amino]benzoate

生成物 1

HCID 15670251Ethyl 3-[(2-mercaptomethyl-3-phenylpropionyl)amino]benzoate収率 28.1%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒2 回

実験手順

Ethyl 3-[(2-acetylthiomethyl-3-phenylpropionyl)-amino]benzoate (compound of Example 68-(a)-[1]) (2.0 g) is dissolved in a 80% aqueous acetonitrile, and thereto is added pyrrolidine (0.5 g), and the mixture is stirred at room temperature for 30 minutes. The mixture is adjusted to pH 5.0 with 10% hydrochloric acid, and acetonitrile is distilled off under reduced pressure, and the residue is extracted with ethyl acetate (50 ml). The extract is washed with water, and ethyl acetate is distilled off under reduced pressure. The 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. The aqueous solution is extracted with ethyl acetate (50 ml), and the extract is dried over anhydrous magnesium sulfate, and ethyl acetate is distilled off under reduced pressure to give the title compound (0.5 g) as an oily substance. IR (film; cm-1): 1710, 1660 Elementary analysis for C19H21NO3S: Calcd. (%): C,66.45; H,6.16; N,4.08; S,9.34 Found (%): C,66.37; H,6.25; N,4.04; S,9.05

後処理

  1. distillationis distilled off under reduced pressure
  2. extractionthe residue is extracted with ethyl acetate (50 ml)
  3. washThe extract is washed with water, and ethyl acetate
  4. distillationis distilled off under reduced pressure
  5. customThe residue is purified by a medium pressure column chromatography with CHP-20P (eluant, water-acetonitrile)
  6. additionThe fractions containing the desired compound
  7. customare collected
  8. distillationacetonitrile is distilled off under reduced pressure
  9. extractionThe aqueous solution is extracted with ethyl acetate (50 ml)
  10. dry with materialthe extract is dried over anhydrous magnesium sulfate, and ethyl acetate
  11. distillationis distilled off under reduced pressure

出典と根拠

ORDレコード
ord-24d07538e90243bcab697813f004f33e
出典データセット
uspto-grants-1993_05
特許番号
US05210266

反応ノート

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