Trifluoroacetic acid → HCID 136352173, compound

HRID 2405035Notes

Reaction equation

HRID 2405035 reaction equation
[CH2:1]([O:8][C:9](=[O:37])[NH:10][CH2:11][C:12](=[O:36])[NH:13][C:14]1[C:18]([C:19]2[N:23](COCC[Si](C)(C)C)[C:22]3[CH:32]=[CH:33][CH:34]=[CH:35][C:21]=3[N:20]=2)=[N:17][O:16][N:15]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>>[CH2:1]([O:8][C:9](=[O:37])[NH:10][CH2:11][C:12](=[O:36])[NH:13][C:14]1[C:18]([C:19]2[NH:23][C:22]3[CH:32]=[CH:33][CH:34]=[CH:35][C:21]=3[N:20]=2)=[N:17][O:16][N:15]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66926198HCID 66926198, compound

Product 1

HCID 136352173HCID 136352173, compoundYield 101.9%

Conditions

Temperature
50 °C

Procedure

0.55 g of ({4-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzoimidazol-2-yl]-furazan-3-ylcarbamoyl}-methyl)-carbamic acid benzyl ester (1.00 mmol; 1 eq.) are added portionwise to 2.75 mL of trifluoroacetic acid (35.3 mmol; 35 eq.) at room temperature. The solution is stirred for 1 h and then concentrated to dryness under reduced pressure. The residue is dissolved in 3 mL of THF. Then, 2 mL of an aqueous solution of 8% sodium hydrogen carbonate are added. The resulting biphasic mixture is heated to 50° C. and vigorously stirred for 1.5 h. Then, the mixture is diluted with 10 mL of ethyl acetate and 5 mL of water and the organic layer is separated, washed with brine (5 mL), dried over magnesium sulfate, filtered and concentrated to dryness under reduced pressure to give 0.4 g of the desired product as a white solid.

Workup

  1. concentrationconcentrated to dryness under reduced pressure
  2. dissolutionThe residue is dissolved in 3 mL of THF
  3. additionThen, 2 mL of an aqueous solution of 8% sodium hydrogen carbonate are added
  4. stirringvigorously stirred for 1.5 h
  5. additionThen, the mixture is diluted with 10 mL of ethyl acetate and 5 mL of water
  6. customthe organic layer is separated
  7. washwashed with brine (5 mL)
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-d3927deca17a4c45adb15add60f02eef
Source dataset
uspto-grants-2014_08
Patent number
US08802858B2

Reaction notes

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