Trifluoroacetic acid → HCID 10936340, compound

HRID 1370327Notes

Reaction equation

HRID 1370327 reaction equation
[N+:1]([C:4]1[C:9]2[C:10](=O)[C:11]3[C:12]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=4[NH:25]C(=O)C(F)(F)F)=[CH:13][CH:14]=[N:15][C:16]=3[C:17](=[O:18])[C:8]=2[N:7]=[CH:6][CH:5]=1)([O-:3])=[O:2].FC(F)(F)C(O)=O>C(Cl)Cl>[N+:1]([C:4]1[CH:5]=[CH:6][N:7]=[C:8]2[C:9]=1[C:10]1[N:25]=[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]3=[C:12]3[CH:13]=[CH:14][N:15]=[C:16]([C:11]=13)[C:17]2=[O:18])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 11037581HCID 11037581, compound

Product 1

HCID 10936340HCID 10936340, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

365 mg (0.826 mmol) of the compound of Example 3 and 2 mL of trifluoroacetic acid in 20 mL of CH2Cl2 are refluxed for 3 hours. After evaporating off the solvent on a rotary evaporator, the residue is taken up in 20 mL of 1N NaOH and 20 mL of CHCl3 and the reaction medium is stirred overnight. The organic phase is recovered and the aqueous phase is extracted with CHCl3 (5 times 20 mL). After drying the organic phases over MgSO4 and evaporating off the solvent on a rotary evaporator, the residue is purified by flash chromatography on a column of RP8 grafted silica (60/40 MeOH/H2O) to give 135 mg of compound in the form of pale orange-yellow crystals.

Workup

  1. customAfter evaporating off the solvent
  2. customon a rotary evaporator
  3. customThe organic phase is recovered
  4. extractionthe aqueous phase is extracted with CHCl3 (5 times 20 mL)
  5. dry with materialAfter drying the organic phases over MgSO4
  6. customevaporating off the solvent
  7. customon a rotary evaporator
  8. customthe residue is purified by flash chromatography on a column of RP8 grafted silica (60/40 MeOH/H2O)

Sources & evidence

ORD record
ord-7c13be0d3af84b1e9a5a511ba28c4ccc
Source dataset
uspto-grants-2003_06
Patent number
US06583150B1

Reaction notes

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