Potassium Iodide → Diethylaminocarbonylmethyl 3-[(2-acetylthiomethyl-3-phenylpropionyl)amino]benzoate

HRID 248702

Reaction equation

HRID 248702 reaction equation
[C:1]([S:4][CH2:5][CH:6]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:7]([NH:9][C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=1)[C:13]([OH:15])=[O:14])=[O:8])(=[O:3])[CH3:2].[I-].[K+].C(N(CC)CC)C.Cl[CH2:36][C:37]([N:39]([CH2:42][CH3:43])[CH2:40][CH3:41])=[O:38]>CN(C=O)C.O>[C:1]([S:4][CH2:5][CH:6]([CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[C:7]([NH:9][C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=1)[C:13]([O:15][CH2:36][C:37]([N:39]([CH2:42][CH3:43])[CH2:40][CH3:41])=[O:38])=[O:14])=[O:8])(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 8471TriethylamineHCID 16844Chloro-N,N-diethylacetamideHCID 10215552Benzoic acid, 3-[[2-[(acetylthio)methyl]-1-oxo-3-phenylpropyl]amino]-

Product 1

HCID 15670248Diethylaminocarbonylmethyl 3-[(2-acetylthiomethyl-3-phenylpropionyl)amino]benzoateYield 74.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

3-[(2-Acetylthiomethyl-3-phenylpropionyl)amino]-benzoic acid (compound of Example 68-(b)-[1]) (0.72 g) and potassium iodide (0.37 g) are dissolved in DMF, and thereto are added triethylamine (0.2 g) and 2-chloro-N,N-diethylacetamide (0.33 g) with stirring at room temperature, and the mixture is reacted three nights. The reaction mixture is mixed with water and extracted with ethyl acetate. The extract is washed with water, dried over anhydrous magnesium sulfate, and ethyl acetate is distilled off under reduced pressure. The residue is purified by a medium pressure column chromatography using silica gel (eluant, chloroform). The fractions containing the desired compound are collected, and chloroform is distilled off under reduced pressure to give the title compound (0.71 g). m.p.: 143°-144° C. (amorphous) IR (KBr; cm-1): 1725, 1690, 1635

Workup

  1. customthe mixture is reacted three nights
  2. extractionextracted with ethyl acetate
  3. washThe extract is washed with water
  4. dry with materialdried over anhydrous magnesium sulfate, and ethyl acetate
  5. distillationis distilled off under reduced pressure
  6. customThe residue is purified by a medium pressure column chromatography
  7. additionThe fractions containing the desired compound
  8. customare collected
  9. distillationchloroform is distilled off under reduced pressure

Sources & evidence

ORD record
ord-bd327e3a4f3a4b43ac7cc8bcd61a6a65
Source dataset
uspto-grants-1993_05
Patent number
US05210266

Linked notes

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