Dichloromethane → HCID 22876217, compound

HRID 1376594Notes

Reaction equation

HRID 1376594 reaction equation
FC(F)(F)[C:3]([NH:5][C@H:6]([C:8]1[N:15]2[C:11]([S:12][CH:13]=[CH:14]2)=[CH:10][N:9]=1)[CH3:7])=[O:4].C(=O)([O-])[O-].[K+].[K+].C(Cl)Cl.C(OC(=O)C)(=O)C>CO.O.C(O)=O>[CH:3]([NH:5][C@H:6]([C:8]1[N:15]2[C:11]([S:12][CH:13]=[CH:14]2)=[CH:10][N:9]=1)[CH3:7])=[O:4]

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 7918Acetic Anhydride2×HCID 11430Potassium Carbonate2×HCID 53726672HCID 53726672, compound

Product 1

HCID 22876217HCID 22876217, compoundYield 93%

Reagents, catalysts & solvents 3

HCID 284Formic AcidSolvent2×HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 1.108 of the above-obtained 5-[(S)-1-(trifluoroacetylamino)ethyl]imidazo[5,1-b]thiazole in 20 ml of methanol was added a solution of 2.70 g of potassium carbonate in 20 ml of water, and the mixture was stirred at room temperature under argon atmosphere for 14 hours. To the reaction solution was added 50 ml of methylene chloride. To this mixture was added with ice-cooling a mixture of 0.50 g of formic acid and 0.25 g of acetic anhydride, which had been heated to 50° C. for 10 minutes and then cooled to room temperature, and the resulting mixture was stirred for an additional 30 minutes. 2.70 g of potassium carbonate was added to this reaction solution to obtain a solution, to which was added again with ice-cooling a mixture of 0.50 g of formic acid and 0.25 g of acetic anhydride, which had been heated to 50° C. for 10 minutes and then cooled to room temperature, and the resulting mixture was stirred for 30 minutes. Insoluble matters were removed by filtration. The organic layer was separated, and the aqueous layer was extracted with methylene chloride (30 ml×2). The combined organic layers were dried over anhydrous potassium carbonate, concentrated under reduced pressure, and purified by flash column chromatography using silica gel, eluting first with ethyl acetate and then with a 20:1 mixture of ethyl acetate and methanol to give 0.763 g (yield 93%) of the title compound.

Workup

  1. additionTo this mixture was added with ice-
  2. temperaturecooling
  3. temperaturehad been heated to 50° C. for 10 minutes
  4. temperaturecooled to room temperature
  5. stirringthe resulting mixture was stirred for an additional 30 minutes
  6. customto obtain a solution
  7. additionto which was added again with ice-
  8. temperaturecooling
  9. temperaturehad been heated to 50° C. for 10 minutes
  10. temperaturecooled to room temperature
  11. stirringthe resulting mixture was stirred for 30 minutes
  12. customInsoluble matters were removed by filtration
  13. customThe organic layer was separated
  14. extractionthe aqueous layer was extracted with methylene chloride (30 ml×2)
  15. dry with materialThe combined organic layers were dried over anhydrous potassium carbonate
  16. concentrationconcentrated under reduced pressure
  17. custompurified by flash column chromatography
  18. washeluting first with ethyl acetate
  19. additionwith a 20:1 mixture of ethyl acetate and methanol

Sources & evidence

ORD record
ord-eb73bfc39f6c4dc7ae1c42b9964e05c1
Source dataset
uspto-grants-1997_09
Patent number
US05663162

Reaction notes

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