Glycolic Acid → HCID 19605073, compound

HRID 1603480Notes

Reaction equation

HRID 1603480 reaction equation
[NH2:1][CH2:2][C:3]1[N:4]2[CH:10]=[N:9][CH:8]=[C:5]2[S:6][CH:7]=1.[C:11](O)(=[O:14])[CH2:12][OH:13].ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1>C1COCC1.CO>[OH:14][CH2:11][C:12]([NH:1][CH2:2][C:3]1[N:4]2[CH:10]=[N:9][CH:8]=[C:5]2[S:6][CH:7]=1)=[O:13]

Participants

7

Reactant 4

HCID 757Glycolic AcidHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 196051553-Aminomethylimidazo[5,1-b]thiazole

Product 1

HCID 19605073HCID 19605073, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixed solution of 4 ml of methanol and 296 mg of THF containing 296 mg of 3-aminomethylimidazo[5,1-b]thiazole, 162 mg of glycolic acid, 26 mg of 1-hydroxybenzotriazole and 439 mg of 1,3-dicyclohexylcarbodiimide were added, and the mixture was then stirred at room temperature for 1 hour. Further, insolubles were removed therefrom by filtration, and after washing with methanol, the filtrate was concentrated under reduced pressure. To the resulting residue, dichloromethane and an aqueous potassium carbonate solution were added, and the crystal was collected by filtration. The organic layer was separated from the filtrate, and the aqueous layer was extracted five times with dichloromethane. The combined organic layer was dried over anhydrous magnesium sulfate and then filtered, and the solvent was evaporated under reduced pressure. The resulting residue was combined with the above crystal, and crystallization was then made from ethyl acetate. To the obtained crystal, 20 ml of water and 2.7 ml of a 1N aqueous hydrochloric acid solution were added, and insolubles were then removed therefrom by filtration. Afterward, anhydrous potassium carbonate was dissolved in the filtrate, and the resulting crystal was collected by filtration, and then washed with dichloromethane and water to obtain 267 mg of the title compound.

Workup

  1. customFurther, insolubles were removed
  2. filtrationby filtration
  3. washafter washing with methanol
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. additionTo the resulting residue, dichloromethane and an aqueous potassium carbonate solution were added
  6. filtrationthe crystal was collected by filtration
  7. customThe organic layer was separated from the filtrate
  8. extractionthe aqueous layer was extracted five times with dichloromethane
  9. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
  10. filtrationfiltered
  11. customthe solvent was evaporated under reduced pressure
  12. customThe resulting residue was combined with the above crystal, and crystallization
  13. additionTo the obtained crystal, 20 ml of water and 2.7 ml of a 1N aqueous hydrochloric acid solution were added
  14. custominsolubles were then removed
  15. filtrationby filtration
  16. dissolutionAfterward, anhydrous potassium carbonate was dissolved in the filtrate
  17. filtrationthe resulting crystal was collected by filtration
  18. washwashed with dichloromethane and water

Sources & evidence

ORD record
ord-5716044f2bfd493f990d199b27ffa9dd
Source dataset
uspto-grants-1999_11
Patent number
US05990101

Reaction notes

Loading…