Ammonia → Benzyl 3-[(2-mercaptomethyl-3-phenylpropionyl)amino]benzoate

HRID 248689

반응식

HRID 248689 반응식
C([S:4][CH2:5][CH:6]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:7]([NH:9][C:10]1[CH:11]=[C:12]([CH:23]=[CH:24][CH:25]=1)[C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])=[O:8])(=O)C.N.Cl>C(#N)C>[SH:4][CH2:5][CH:6]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:7]([NH:9][C:10]1[CH:11]=[C:12]([CH:23]=[CH:24][CH:25]=1)[C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])=[O:8]

참가 물질

5

반응물 3

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 15670217Benzyl 3-[(2-acetylthiomethyl-3-phenylpropionyl)amino]benzoate

생성물 1

HCID 15670210Benzyl 3-[(2-mercaptomethyl-3-phenylpropionyl)amino]benzoate수율 49.7%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

Benzyl 3-[(2-acetylthiomethyl-3-phenylpropionyl)-amino]benzoate (2.0 g) is dissolved in acetonitrile (20 ml), and thereto is added 28% aqueous ammonia (15 ml), and the mixture is stirred at room temperature for one hour. The reaction mixture is adjusted to pH 2.5 with 20% hydrochloric acid under ice cooling and is extracted with ethyl acetate (70 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 and the residue is extracted with ethyl acetate (100 ml). The extract is dried over anhydrous magnesium sulfate, and ethyl acetate is distilled off under reduced pressure to give the title compound (0.9 g) as a colorless oily substance.

후처리

  1. extractionis extracted with ethyl acetate (70 ml)
  2. washThe extract is washed with water, and ethyl acetate
  3. distillationis distilled off under reduced pressure
  4. customThe residue is purified by a medium pressure column chromatography with CHP-20P (eluant, water-acetonitrile)
  5. additionThe fractions containing the desired compound
  6. customare collected
  7. distillationacetonitrile is distilled off under reduced pressure
  8. extractionthe residue is extracted with ethyl acetate (100 ml)
  9. dry with materialThe extract is dried over anhydrous magnesium sulfate, and ethyl acetate
  10. distillationis distilled off under reduced pressure

출처 및 근거

ORD 기록
ord-2ad6f8f61d8345da8659d197028f2151
출처 데이터셋
uspto-grants-1993_05
특허 번호
US05210266

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