Trifluoroacetic acid → HCID 19605015, compound

HRID 1603483Notes

Reaction equation

HRID 1603483 reaction equation
FC(F)(F)C(O)=O.[C:8]([O:11][CH2:12][C:13]1[S:17][C:16]([CH2:18][NH:19][C:20](OC(C)(C)C)=[O:21])=[N:15][CH:14]=1)(=[O:10])[CH3:9]>>[C:8]([O:11][CH2:12][C:13]1[S:17][C:16]([CH2:18][NH:19][CH:20]=[O:21])=[N:15][CH:14]=1)(=[O:10])[CH3:9]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 19605151HCID 19605151, compound

Product 1

HCID 19605015HCID 19605015, compoundYield 94.5%

Procedure

A 8 ml potion of trifluoroacetic acid was dissolved in 2.46 g of 5-acetoxymethyl-2-(N-t-butoxycarbonylamino)methylthiazole under ice-cooling, and the mixture was then allowed to stand at room temperature for 1 hour. Then, the solvent was evaporated under reduced pressure, and the resulting residue was dissolved in 24.6 ml of dichloromethane under ice-cooling. Furthermore, 40 ml of an aqueous saturated sodium bicarbonate solution was added thereto, followed by stirring. To this solution, a 10% aqueous sodium carbonate solution and a mixed acid anhydride solution comprising a mixed solution of 3.7 ml of formic acid and 2.0 ml of acetic anhydride which had been beforehand reacted with each other at 50° C. for 30 minutes were added dropwise under ice-cooling so that the pH of the reaction solution might be within the range of 3.0 to 6.5. Afterward, the organic layer was separated, and the remaining aqueous layer was concentrated under reduced pressure until its amount became half, followed by extraction with chloroform (15 ml×4). The combined organic layer was dried over anhydrous sodium sulfate and then filtered, and the solvent was evaporated under reduced pressure to obtain 1.74 g of 5-acetoxymethyl-2-(formylamino)methylthiazole.

Workup

  1. temperaturecooling
  2. customThen, the solvent was evaporated under reduced pressure
  3. dissolutionthe resulting residue was dissolved in 24.6 ml of dichloromethane under ice-
  4. temperaturecooling
  5. additionFurthermore, 40 ml of an aqueous saturated sodium bicarbonate solution was added
  6. customhad been beforehand reacted with each other at 50° C. for 30 minutes
  7. additionwere added dropwise under ice-
  8. temperaturecooling so that the pH of the reaction solution
  9. customAfterward, the organic layer was separated
  10. concentrationthe remaining aqueous layer was concentrated under reduced pressure until its amount
  11. extractionfollowed by extraction with chloroform (15 ml×4)
  12. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  13. filtrationfiltered
  14. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-34614b6614fd4ff88d386672b91730cd
Source dataset
uspto-grants-1999_11
Patent number
US05990101

Reaction notes

Loading…