Trifluoroacetic acid → HCID 9882927, compound

HRID 351139Notes

Reaction equation

HRID 351139 reaction equation
[C:1]1([CH2:7][C:8]([NH:10][CH2:11][CH2:12][C:13]2[CH:14]=[CH:15][CH:16]=[C:17]3[C:22]=2[CH:21]=[C:20](C(Cl)=O)[CH:19]=[CH:18]3)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N-:26]=[N+]=[N-].[Na+].FC(F)(F)C(O)=O.C(=O)([O-])[O-].[K+].[K+]>ClCCl.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[NH2:26][C:20]1[CH:21]=[C:22]2[C:17]([CH:16]=[CH:15][CH:14]=[C:13]2[CH2:12][CH2:11][NH:10][C:8](=[O:9])[CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:18][CH:19]=1

Participants

8

Reactant 4

HCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 33557Sodium AzideHCID 21917114HCID 21917114, compound

Product 1

HCID 9882927HCID 9882927, compound

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of the product obtained in Step D (20 mmol) in dichloromethane (30 ml) containing tetrabutylammonium bromide (20 mg) is cooled in an ice bath. After adding sodium azide (24 mmol) dissolved in 5 ml of water, the solution is stirred vigorously at 0° C. for 2 hours. The organic phase is separated off, washed with water (2×5 ml) and dried over magnesium sulphate. After filtration, trifluoroacetic acid (30 mmol) is added and the solution is stirred under reflux for 60 hours. After cooling, the organic phase is washed with saturated sodium hydrogen carbonate solution (2×5 ml) and is concentrated under reduced pressure. The residue is then taken up in methanol (20 ml); water (80 ml) and then potassium carbonate (30 mmol) are added. After stirring at ambient temperature for 20 hours, the reaction mixture is concentrated under reduced pressure to a volume of about 60 ml and is then extracted 3 times with ether (3×50 ml). After drying over sodium sulphate, the organic phase is filtered and then evaporated under reduced pressure. The residue is chromatographed on silica gel to yield the title product.

Workup

  1. temperatureis cooled in an ice bath
  2. customThe organic phase is separated off
  3. washwashed with water (2×5 ml)
  4. dry with materialdried over magnesium sulphate
  5. additionis added
  6. stirringthe solution is stirred
  7. temperatureunder reflux for 60 hours
  8. temperatureAfter cooling
  9. washthe organic phase is washed with saturated sodium hydrogen carbonate solution (2×5 ml)
  10. concentrationis concentrated under reduced pressure
  11. stirringAfter stirring at ambient temperature for 20 hours
  12. concentrationthe reaction mixture is concentrated under reduced pressure to a volume of about 60 ml
  13. extractionis then extracted 3 times with ether (3×50 ml)
  14. dry with materialAfter drying over sodium sulphate
  15. filtrationthe organic phase is filtered
  16. customevaporated under reduced pressure
  17. customThe residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-02142f15fe9d48a481c864c0aacc50a3
Source dataset
uspto-grants-2007_02
Patent number
US07183318B2

Reaction notes

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