Hydrochloric Acid → HCID 15670284, compound

HRID 248707Notes

Reaction equation

HRID 248707 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].Cl[C:25]([O:27][CH2:28][CH:29]([CH3:31])[CH3:30])=[O:26].Cl>C(=O)([O-])O.[Na+].O1CCCC1>[CH2:28]([O:27][C:25]([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:26])[CH:29]([CH3:31])[CH3:30]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 62365Isobutyl chloroformateHCID 15670155HCID 15670155, compound

Product 1

HCID 15670284HCID 15670284, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

3-[(2-Mercaptomethyl-3-phenylpropionyl)amino]-2-methylbenzoic acid (compound of Example 7) (0.66 g) is dissolved in a mixture of saturated aqueous sodium hydrogen carbonate solution and tetrahydrofuran (1 ml), and to the mixture is added a solution of isobutyl chloroformate (0.33 g) in tetrahydrofuran (5 ml) with stirring under ice cooling, and the mixture is stirred under ice cooling for 30 minutes and further at room temperature for one hour. The reaction mixture is acidified with 4N hydrochloric acid and extracted with ethyl acetate. The extract is washed with water and dried over anhydrous magnesium sulfate, and the solvent 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 (0.31 g). m.p.: 165°-167° C. (amorphous) IR (KBr; cm-1): 1700, 1650

Workup

  1. stirringthe mixture is stirred under ice cooling for 30 minutes and further at room temperature for one hour
  2. extractionextracted with ethyl acetate
  3. washThe extract is washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent is distilled off under reduced pressure
  6. customThe residue is purified by a medium pressure column chromatography with CHP-20P (eluant, water-acetonitrile)
  7. additionThe fractions containing the desired compound
  8. customare collected
  9. concentrationconcentrated under reduced pressure
  10. customthe precipitates are separated by filtration

Sources & evidence

ORD record
ord-4d670f974d4a4e778839b8f9b4f86825
Source dataset
uspto-grants-1993_05
Patent number
US05210266

Reaction notes

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