Dimethylcarbamoyl Chloride → HCID 15670280, compound

HRID 248706Notes

Reaction equation

HRID 248706 reaction equation
[SH:1][CH2:2][CH:3]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:4]([NH:6][C:7]1[C:8]([CH3:16])=[C:9]([CH:13]=[CH:14][CH:15]=1)[C:10]([OH:12])=[O:11])=[O:5].[CH3:24][N:25]([CH3:29])[C:26](Cl)=[O:27].C(OCC)(=O)C>N1C=CC=CC=1>[CH3:24][N:25]([CH3:29])[C:26]([S:1][CH2:2][CH:3]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:4]([NH:6][C:7]1[C:8]([CH3:16])=[C:9]([CH:13]=[CH:14][CH:15]=1)[C:10]([OH:12])=[O:11])=[O:5])=[O:27]

Participants

5

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 8857Ethyl AcetateHCID 15670155HCID 15670155, compound

Product 1

HCID 15670280HCID 15670280, compoundYield 28.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3-[(2-Mercaptomethyl-3-phenylpropionyl)amino-2-methylbenzoic acid (compound of Example 7) (0.66 g) is dissolved in pyridine (2 ml), and thereto is added dimethylaminocarbonyl chloride (0.26 g) with stirring under ice cooling, and the mixture is stirred under ice cooling for 2 hours and further at room temperature for 2 hours. To the reaction mixture is added ethyl acetate (50 ml) and the mixture is washed with saturated aqueous citric acid solution and 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 with CHP-20P (eluant, water-acetonitrile). The fractions containing the desired compound are collected and concentrated under reduced pressure, and the precipitates are separated by filtration to give the title compound (0.23 g). m.p.: 84°-87° C. (amorphous) IR (KBr; cm-1): 1710, 1690, 1650

Workup

  1. stirringthe mixture is stirred under ice cooling for 2 hours and further at room temperature for 2 hours
  2. washthe mixture is washed with saturated aqueous citric acid solution and water
  3. dry with materialdried over anhydrous magnesium sulfate, 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. concentrationconcentrated under reduced pressure
  9. customthe precipitates are separated by filtration

Sources & evidence

ORD record
ord-99ea6ad12f664c80a04a10439be5feb9
Source dataset
uspto-grants-1993_05
Patent number
US05210266

Reaction notes

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