Trifluoroacetic anhydride → HCID 23296632, compound

HRID 1954407Notes

Reaction equation

HRID 1954407 reaction equation
[C:1]([CH2:3][CH2:4][NH:5][C:6](=O)[CH2:7][Br:8])#[N:2].[N-:10]=[N+:11]=[N-:12].[Na+].FC(F)(F)C(OC(=O)C(F)(F)F)=O.C(=O)([O-])O.[Na+]>C(Cl)Cl>[Br:8][CH2:7][C:6]1[N:5]([CH2:4][CH2:3][C:1]#[N:2])[N:12]=[N:11][N:10]=1

Participants

6

Reactant 4

HCID 9845Trifluoroacetic anhydrideHCID 33557Sodium AzideHCID 516892Sodium BicarbonateHCID 12973192HCID 12973192, compound

Product 1

HCID 23296632HCID 23296632, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1.50 g (7.85 mmol) of bromoacetic acid-(2-cyanoethyl)-amide are dissolved in 50 ml of methylene chloride and mixed with 508 mg (7.85 mmol) of sodium azide. At 0° C. a solution of 2.20 g (7.85 mmol) of trifluoroacetic acid anhydride in 5 ml of methylene chloride is added dropwise. After 22 hours at ambient temperature saturated sodium hydrogen carbonate solution is added and the resulting mixture is extracted 3 x with methylene chloride. The combined organic phases are dried over sodium sulphate and concentrated by evaporation. The crude product is chromatographed on silica gel, eluting first with methylene chloride, later with methylene chloride/ethanol (50:1). The desired fractions are combined and concentrated by evaporation.

Workup

  1. extractionthe resulting mixture is extracted 3 x with methylene chloride
  2. dry with materialThe combined organic phases are dried over sodium sulphate
  3. concentrationconcentrated by evaporation
  4. customThe crude product is chromatographed on silica gel
  5. washeluting first with methylene chloride, later with methylene chloride/ethanol (50:1)
  6. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-e405441816f24433b732e50256e0698c
Source dataset
uspto-grants-2000_09
Patent number
US06121308

Reaction notes

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