Hydrochloric Acid → HCID 14129803, compound

HRID 1252078Notes

Reaction equation

HRID 1252078 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]2[CH2:15][CH2:14][N:13]([CH2:16][C:17]3[N:18]=[C:19]([NH:22][C:23](=[O:30])[C@H:24]([O:26]C(=O)C)[CH3:25])[S:20][CH:21]=3)[CH2:12][CH2:11]2)=[CH:2]1.[OH-].[Na+].Cl>C(O)C>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]2[CH2:11][CH2:12][N:13]([CH2:16][C:17]3[N:18]=[C:19]([NH:22][C:23](=[O:30])[C@@H:24]([CH3:25])[OH:26])[S:20][CH:21]=3)[CH2:14][CH2:15]2)=[CH:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 14129791HCID 14129791, compound

Product 1

HCID 14129803HCID 14129803, compoundYield 43.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In ethanol (5 ml) was dissolved 4-[4-(3-indolyl)piperidinomethyl]-2-[(2R)-2-acetoxypropionylamino]thiazole (1 g) and under ice-cooling, 1N aqueous sodium hydroxide solution (2.34 ml) was added. The mixture was stirred for 1 hour at the same temperature and, then, for 1.5 hours at ambient temperature. Thereafter, 1N aqueous sodium hydroxide solution (0.7 ml) was further added and the mixture was stirred at ambient temperature for another 2 hours. The reaction mixture was then neutralized with 1N hydrochloric acid and concentrated under reduced pressure. The residue was extracted with a mixture of chloroform and methanol (10:1 V/V) and the extract was washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to column chromatography on silica gel and elution was carried out with a mixture of chloroform and methanol (10:1 V/V) to give 4-[4-(3-indolyl)piperidinomethyl]-2-(D-lactoylamino)thiazole (0.39 g).

Workup

  1. temperatureunder ice-cooling
  2. waitfor 1.5 hours at ambient temperature
  3. stirringthe mixture was stirred at ambient temperature for another 2 hours
  4. concentrationconcentrated under reduced pressure
  5. extractionThe residue was extracted with a mixture of chloroform and methanol (10:1 V/V)
  6. washthe extract was washed with a saturated aqueous solution of sodium chloride
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. washThe residue was subjected to column chromatography on silica gel and elution
  10. additionwas carried out with a mixture of chloroform and methanol (10:1 V/V)

Sources & evidence

ORD record
ord-5111097175834745a4a6244d58f423b6
Source dataset
uspto-grants-1988_05
Patent number
US04742057

Reaction notes

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