Hydrochloric Acid → HCID 58124096, compound

HRID 872168Notes

Reaction equation

HRID 872168 reaction equation
[C:1]([C:5]1[CH:6]=[CH:7][C:8]([CH2:14][NH:15]C(N(C)C)=O)=[C:9]([CH:13]=1)[C:10](O)=[O:11])([CH3:4])([CH3:3])[CH3:2].Cl.C(=O)([O-])[O-].[K+].[K+]>FC(F)(F)C(O)=O>[C:1]([C:5]1[CH:13]=[C:9]2[C:8]([CH2:14][NH:15][C:10]2=[O:11])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 86697940HCID 86697940, compound

Product 1

HCID 58124096HCID 58124096, compoundYield 29.3%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A 500-mL, round-bottomed flask equipped with a magnetic stirrer and reflux condenser was charged with 107b (3.97 g, 14.2 mmol) and 12.1 N hydrochloric acid (100 mL) and heated to reflux. Trifluoroacetic acid (40 mL) was added and the reaction was refluxed overnight. After this time, the mixture was carefully neutralized to pH 7.5 with potassium carbonate (approximately 67 g) and then extracted with methyl t-butyl ether ((100 mL) and ethyl acetate (3×50 mL). The organic layers were combined, dried over sodium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by column chromatography to afford a 29% yield (788 mg) of 107c as a white solid: mp 142-144° C.; 1H NMR (500 MHz, CDCl3) δ 7.92 (d, J=1.5 Hz, 1H), 7.64 (dd, J=8.5, 2.0 Hz, 1H), 7.42 (dd, J=8.0, 0.5 Hz, 1H), 6.58 (s, 1H), 4.42 (s, 2H), 1.37 (s, 9H); MS (ESI+) m/z 190.1 (M+H).

Workup

  1. customA 500-mL, round-bottomed flask equipped with a magnetic stirrer
  2. temperaturereflux condenser
  3. temperatureheated to reflux
  4. temperaturethe reaction was refluxed overnight
  5. extractionextracted with methyl t-butyl ether ((100 mL) and ethyl acetate (3×50 mL)
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under reduced pressure
  9. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-af1b6ebcaaa448ceac272e035eeefa6d
Source dataset
uspto-grants-2015_03
Patent number
US08975260B2

Reaction notes

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