Diethyl Ether → HCID 22104483, compound

HRID 1457332Notes

Reaction equation

HRID 1457332 reaction equation
CO[C:3](=[O:25])[C@@H:4]1[CH2:8][CH2:7][CH2:6][N:5]1[C:9](=[O:24])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16](=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[F:26][C:27]([F:32])([F:31])C(O)=O.FC(F)(F)C(OC(=O)C(F)(F)F)=O.CCOCC>C(Cl)Cl>[C:16]([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[C:9]([N:5]1[CH2:6][CH2:7][CH2:8][CH:4]1[C:3](=[O:25])[C:27]([F:32])([F:31])[F:26])=[O:24])(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6422Trifluoroacetic acidHCID 9845Trifluoroacetic anhydrideHCID 53808064HCID 53808064, compound

Product 1

HCID 22104483HCID 22104483, compoundYield 2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4.0 g (10.6 mmol) of the title compound of Example 25 was dissolved in 50 ml of methylene chloride at room temperature under an atmosphere of nitrogen. 20 ml (260 mmol) trifluoroacetic acid (TFA) was added and the solution refluxed for 2 hours to hydrolyze the ester. Solvent and excess TFA were then removed under reduced pressure, the residue was redissolved in 22.5 ml (159 mmol) of trifluoroacetic anhydride (TFAA), and the solution ref luxed for 12 hours. The TFAA was evaporated under high vacuum at 80° C. to give an impure yellow gum. Flash chromatography on silica gel with 100% ether afforded 80 mg (2%) of the title compound as a yellow foam. TLC (Ether): Rf =0.50. 1H NMR (CDCl3) δ: 7.32-7.84(m,9H); 4.30-4.96(m,1H); 3.20-3.54 (M,2H); 1.68-2.48(m,4H). High Resolution Mass Spectrum: 376.1170±0.9 ppm (calculated for C20H17NO3F3). 2,4-DNP test: positive

Workup

  1. temperaturethe solution refluxed for 2 hours
  2. customSolvent and excess TFA were then removed under reduced pressure
  3. customThe TFAA was evaporated under high vacuum at 80° C.
  4. customto give an impure yellow gum

Sources & evidence

ORD record
ord-d855b655774e4d5a875e5365bb0dad97
Source dataset
uspto-grants-1998_12
Patent number
US05847155

Reaction notes

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