Hydrochloric Acid → HCID 15670308, compound

HRID 248710Notes

Reaction equation

HRID 248710 reaction equation
C([S:4][CH2:5][CH:6]([CH2:20][CH:21]([CH3:23])[CH3:22])[C:7]([NH:9][C:10]1[C:11]([CH3:19])=[C:12]([CH:16]=[CH:17][CH:18]=1)[C:13]([OH:15])=[O:14])=[O:8])(=O)C.N1CCCC1.Cl>CO>[SH:4][CH2:5][CH:6]([CH2:20][CH:21]([CH3:23])[CH3:22])[C:7]([NH:9][C:10]1[C:11]([CH3:19])=[C:12]([CH:16]=[CH:17][CH:18]=1)[C:13]([OH:15])=[O:14])=[O:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 31268PyrrolidineHCID 15670296HCID 15670296, compound

Product 1

HCID 15670308HCID 15670308, compoundYield 76.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

3-[(2-Acetylthiomethyl-4-methylpentanoyl)amino]-2-methylbenzoic acid (compound of Example 175) (3 g), 70% aqueous methanol (30 ml) and pyrrolidine (2.2 g) are mixed, and the mixture is stirred at room temperature for 30 minutes. The reaction mixture is adjusted to pH 3.0 with 10% hydrochloric acid, and methanol is distilled off under reduced pressure. The precipitated crystals are separated by filtration and dissolved in 50% aqueous acetonitrile and purified by a column chromatography using Diaion HP-20 (eluant, water-acetonitrile). The fractions containing the desired compound are collected and acetonitrile is distilled off under reduced pressure, and the precipitated crystals are separated by filtration to give the title compound (2 g). m.p.: 166°-168° C. (colorless needles) IR (KBr; cm-1): 1690, 1660

Workup

  1. distillationis distilled off under reduced pressure
  2. customThe precipitated crystals are separated by filtration
  3. dissolutiondissolved in 50% aqueous acetonitrile
  4. custompurified by a column chromatography
  5. additionThe fractions containing the desired compound
  6. customare collected
  7. distillationacetonitrile is distilled off under reduced pressure
  8. customthe precipitated crystals are separated by filtration

Sources & evidence

ORD record
ord-4ec466d2b8f649d2a7fca421157f7e39
Source dataset
uspto-grants-1993_05
Patent number
US05210266

Reaction notes

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