Trifluoroacetic acid → HCID 70282403, compound

HRID 976142Notes

Reaction equation

HRID 976142 reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:20][CH2:19][CH:18](/[CH:21]=[CH:22]/[C:23]([C:25]2[CH:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[CH:27][CH:26]=2)=[O:24])[CH2:17][CH2:16]1)=O)(C)(C)C>C(Cl)Cl>[NH:15]1[CH2:20][CH2:19][CH:18](/[CH:21]=[CH:22]/[C:23]([C:25]2[CH:26]=[CH:27][C:28]([N+:31]([O-:33])=[O:32])=[CH:29][CH:30]=2)=[O:24])[CH2:17][CH2:16]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 70281943HCID 70281943, compound

Product 1

HCID 70282403HCID 70282403, compoundYield 38.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3 ml of trifluoroacetic acid was added to 2.52 g of (E)-4-[3-(1-t-butoxycarbonylpiperidin-4-yl)propenoyl]nitrobenzene dissolved in 20 ml of methylene chloride, and the mixture was stirred at room temperature for 3 hours. Subsequently, 7 ml of trifluoroacetic acid was further added to the mixture, and the mixture was stirred for 3 hours. Then, the solvent was removed by distillation, and a saturated sodium hydrogen carbonate solution was added to the residue. After the mixture was extracted with ethyl acetate, the extract was dried over anhydrous sodium sulfate and condensed. The obtained solid was washed with methylene chloride to obtain 0.7 g of the title compound as pale yellow powder.

Workup

  1. stirringthe mixture was stirred for 3 hours
  2. customThen, the solvent was removed by distillation
  3. additiona saturated sodium hydrogen carbonate solution was added to the residue
  4. extractionAfter the mixture was extracted with ethyl acetate
  5. dry with materialthe extract was dried over anhydrous sodium sulfate and condensed
  6. washThe obtained solid was washed with methylene chloride

Sources & evidence

ORD record
ord-c15d0f208cb4446cbaf1c70e728c0beb
Source dataset
uspto-grants-1997_03
Patent number
US05610303

Reaction notes

Loading…