Trifluoroacetic acid → HCID 23725533, compound

HRID 2219422Notes

Reaction equation

HRID 2219422 reaction equation
C([O:8][CH2:9][C:10]1[N:11]([C:27]2[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][CH:28]=2)[CH:12]=[C:13]([C:15]2[C:16]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[N:17][O:18][C:19]=2[CH3:20])[N:14]=1)C1C=CC=CC=1.FC(F)(F)C(O)=O.FC(F)(F)S(O)(=O)=O.C(=O)([O-])O.[Na+]>C(Cl)Cl>[CH3:20][C:19]1[O:18][N:17]=[C:16]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:15]=1[C:13]1[N:14]=[C:10]([CH2:9][OH:8])[N:11]([C:27]2[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][CH:28]=2)[CH:12]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 62406Trifluoromethanesulfonic acidHCID 516892Sodium BicarbonateHCID 23725485HCID 23725485, compound

Product 1

HCID 23725533HCID 23725533, compoundYield 56.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-[2-benzyloxymethyl-1-(4-nitro-phenyl)-1H-imidazol-4-yl]-5-methyl-3-phenyl-isoxazole (200 mg, 0.43 mmol) in DCM (10 mL) at 0° C. was added trifluoroacetic acid (0.98 mL) and trifluoromethanesulfonic acid (0.06 mL) and the resulting mixture stirred vigorously for 3 h. The mixture was then poured onto a saturated solution of sodium hydrogen carbonate and stirred for 30 min. The resulting precipitate was then filtered off, washed with water and then dried to afford the title compound (91 mg, 56%) which was obtained as a white solid. MS: m/e=377.4 [M+H]+.

Workup

  1. stirringstirred for 30 min
  2. filtrationThe resulting precipitate was then filtered off
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-a3aeaa1e9b3c46b8a3f0f115e393a41a
Source dataset
uspto-grants-2008_08
Patent number
US07414061B2

Reaction notes

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