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

HRID 1646296

Reaction equation

HRID 1646296 reaction equation
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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-468e9acc093744328cd20318874bb268
Source dataset
uspto-grants-1993_01
Patent number
US05179125

Linked notes

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