Trifluoroacetic acid → HCID 86270805, compound

HRID 2170209Notes

Reaction equation

HRID 2170209 reaction equation
[F:1][C:2]1[CH:41]=[C:40]([F:42])[CH:39]=[CH:38][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][C:6]=1[C:15]1[N:16](COCC[Si](C)(C)C)[C:17]([CH3:29])=[C:18]2[C:23]=1[CH:22]=[C:21]([C:24]([NH:26][CH3:27])=[O:25])[NH:20][C:19]2=[O:28].C(O)(C(F)(F)F)=O.C([O-])(=O)C.[Na+]>ClCCl>[F:1][C:2]1[CH:41]=[C:40]([F:42])[CH:39]=[CH:38][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:12])[F:13])=[CH:7][C:6]=1[C:15]1[NH:16][C:17]([CH3:29])=[C:18]2[C:23]=1[CH:22]=[C:21]([C:24]([NH:26][CH3:27])=[O:25])[NH:20][C:19]2=[O:28]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 517045Sodium AcetateHCID 90386765HCID 90386765, compound

Product 1

HCID 86270805HCID 86270805, compoundYield 22.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Example 34d (0.023 g, 0.038 mmol) in dichloromethane was added TFA (0.5 mL, 6.49 mmol). The reaction mixture was stirred at ambient temperature for 1 hour and then concentrated by rotary evaporation. The residue was concentrated down from toluene (2×), then taken up in methanol/tetrahydrofuran. Sodium acetate (0.124 g, 1.514 mmol) was added, and the reaction mixture was heated at reflux for 2 hours. The reaction mixture was concentrated by rotary evaporation. The residue was partitioned between ethyl acetate and water. The layers were separated, and the organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated. The crude material was purified by flash chromatography (silica gel, 20-80% ethyl acetate in hexanes) to give the title compound (0.004 g, 22% yield). 1H NMR (300 MHz, DMSO-d6) δ 12.20-12.46 (m, 1 H), 9.06 (s, 1 H), 8.41-8.52 (m, 1 H), 7.82 (d, J=2.03 Hz, 1 H), 7.66 (dd, J=8.82, 1.70 Hz, 1 H), 7.44-7.54 (m, 2 H), 7.15-7.23 (m, 2 H), 6.99 (d, J=8.48 Hz, 1 H), 2.74 (d, J=4.41 Hz, 3 H), 2.65 (s, 3H). MS (ESI+) m/z 478.0)+.

Workup

  1. concentrationconcentrated by rotary evaporation
  2. concentrationThe residue was concentrated down from toluene (2×)
  3. temperaturethe reaction mixture was heated
  4. temperatureat reflux for 2 hours
  5. concentrationThe reaction mixture was concentrated by rotary evaporation
  6. customThe residue was partitioned between ethyl acetate and water
  7. customThe layers were separated
  8. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe crude material was purified by flash chromatography (silica gel, 20-80% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-7e610df3657d403484e30b0757e3e042
Source dataset
uspto-grants-2015_06
Patent number
US09050346B2

Reaction notes

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