Trifluoroacetic acid → HCID 54455605, compound

HRID 583425Notes

Reaction equation

HRID 583425 reaction equation
FC(F)(F)C(O)=O.[CH2:8]([O:10][C:11](=[O:37])[CH:12]=[CH:13][CH:14]([N:28](C(OC(C)(C)C)=O)[CH3:29])[CH:15]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH3:9]>C(Cl)Cl>[CH2:8]([O:10][C:11](=[O:37])[CH:12]=[CH:13][CH:14]([NH:28][CH3:29])[CH:15]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[CH3:9]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 54160597HCID 54160597, compound

Product 1

HCID 54455605HCID 54455605, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

22 ml (0.28 mol) of trifluoroacetic acid are added dropwise to a solution of 14.2 g (34.7 mmol) of 4-(tert-butoxycarbonyl-methyl-amino)-5,5-diphenyl-pent-2-enoic acid ethyl ester in 100 ml of methylene chloride. After 5 hours the reaction mixture is concentrated by evaporation and then twice toluene is added and the mixture concentrated by evaporation. The residue is dissolved in methylene chloride, washed with saturated sodium hydrogen carbonate solution, dried over sodium sulfate and again concentrated by evaporation. The title compound is obtained in the form of a yellow oil. TLC: methylene chloride/methanol (95:5) Rf =0.26; Rt (HPLC)=12.5 min; 1H-NMR (300 MHz, CDCl3, RT) d 7.38-7.15 (m, 10H), 6.66 (dd, 1H), 5.84 (d, 1H), 4.12 (q, 2H), 3.97 (d, 1H), 3.81 (m, 1H), 2.31 (s, 3H), 1.33 (br, 1H), 1.24 (t, 3H).

Workup

  1. concentrationAfter 5 hours the reaction mixture is concentrated by evaporation
  2. additiontwice toluene is added
  3. concentrationthe mixture concentrated by evaporation
  4. dissolutionThe residue is dissolved in methylene chloride
  5. washwashed with saturated sodium hydrogen carbonate solution
  6. dry with materialdried over sodium sulfate
  7. concentrationagain concentrated by evaporation

Sources & evidence

ORD record
ord-acd22f65a43845bc97a72dd1657714ac
Source dataset
uspto-grants-1999_07
Patent number
US05929067

Reaction notes

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