Hydrochloric Acid → Colchicine, N-deacetyl-10-thio-

HRID 2417000Notes

Reaction equation

HRID 2417000 reaction equation
CC([NH:4][C@@H:5]1[C:21]2[C:14](=[CH:15][CH:16]=[C:17]([S:22][CH3:23])[C:18]([CH:20]=2)=[O:19])[C:13]2[C:8](=[CH:9][C:10]([O:28][CH3:29])=[C:11]([O:26][CH3:27])[C:12]=2[O:24][CH3:25])[CH2:7][CH2:6]1)=O.Cl>CO>[CH3:29][O:28][C:10]1[CH:9]=[C:8]2[CH2:7][CH2:6][C@H:5]([NH2:4])[C:21]3[C:14](=[CH:15][CH:16]=[C:17]([S:22][CH3:23])[C:18]([CH:20]=3)=[O:19])[C:13]2=[C:12]([O:24][CH3:25])[C:11]=1[O:26][CH3:27]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 17648Thiocolchicine

Product 1

HCID 17649Colchicine, N-deacetyl-10-thio-Yield 50.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The reaction mixture of thiocolchicine (705 mg, 1.7 mmol), methanol (20 ml) and 2N hydrochloride (20 ml) was refluxed for 24 h. After cooling, the mixture was concentrated in vacuo. After water layer was acidified with sodium hydroxide solution to pH 10, it was extracted with chloroform. Organic layer was washed with water and brine, dried over MgSO4. After removal of the solvent, the residue was separated by column chromatography (eluent: ethyl acetate and ethanol) to give 320 mg N-deacetylthiocolchicine, mp 168-170° C.

Workup

  1. temperaturewas refluxed for 24 h
  2. temperatureAfter cooling
  3. concentrationthe mixture was concentrated in vacuo
  4. extractionwas extracted with chloroform
  5. washOrganic layer was washed with water and brine
  6. dry with materialdried over MgSO4
  7. customAfter removal of the solvent
  8. customthe residue was separated by column chromatography (eluent: ethyl acetate and ethanol)

Sources & evidence

ORD record
ord-79eae18d058d4d808e03ef18dcf16f8f
Source dataset
uspto-grants-2004_11
Patent number
US06825236B2

Reaction notes

Loading…