Hydrochloric Acid → HCID 21999561, compound

HRID 1976941Notes

Reaction equation

HRID 1976941 reaction equation
[OH-:1].[Na+].[OH:3][C:4]1[C:22]([F:23])=[C:21]([OH:24])[C:20]([F:25])=[C:19]([F:26])[C:5]=1[C:6]([C:8]1[C:13](F)=[C:12]([F:15])[C:11](F)=[C:10]([F:17])[C:9]=1[F:18])=[O:7].O.Cl.[CH3:29]O>C(O)(C)C>[CH3:29][O:24][C:21]1[C:20]([F:25])=[C:19]([F:26])[C:5]2[C:6](=[O:7])[C:8]3[C:13]([O:3][C:4]=2[C:22]=1[F:23])=[C:12]([F:15])[C:11]([OH:1])=[C:10]([F:17])[C:9]=3[F:18]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 887Methanol2×HCID 962WaterHCID 14798Sodium HydroxideHCID 21999543HCID 21999543, compound

Product 1

HCID 21999561HCID 21999561, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of sodium hydroxide (125 mg, 3.14 mmol) in 5 mL methanol is added dropwise to a solution of Compound 46 (450 mg, 1.25 mmol) in 10 mL methanol. The reaction mixture is then heated at reflux for 15 hours. The reaction mixture is then poured into 50 mL water and hydrochloric acid is added to a solution pH of 2, and the resulting solution is extracted with ethyl acetate (50 mL×2). The combined organic layers are washed with brine (30 mL), dried over magnesium sulfate and concentrated in vacuo to yield 387 mg (88%) of crude Compound 47. An analytically pure sample is obtained by recrystallization from isopropyl alcohol. mp: 270-272° C. dec. 1H-NMR (d6-DMSO) 4.23 (s). 19F-NMR (d6-DMSO) 141.39 (dd, J=13.0, 20.3 Hz, 1F); 141.85 (dd, J=11.4, 21.6 Hz, 1F); 151.65 (d, J=10.4 Hz, 1F); 154.34 (d, J=20.3 Hz, 1F); 155.46 (t, J=7.9 Hz, 1F); 156.68 (dd, J=6.4, 20.3 Hz, 1F). Anal. calc. for C14H4F6O4: C, 48.02; H, 1.15. Found: C, 47.09; H, 1.07.

Workup

  1. temperatureThe reaction mixture is then heated
  2. temperatureat reflux for 15 hours
  3. extractionthe resulting solution is extracted with ethyl acetate (50 mL×2)
  4. washThe combined organic layers are washed with brine (30 mL)
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customto yield 387 mg (88%) of crude Compound 47

Sources & evidence

ORD record
ord-133ddbd32ec3436db8fd52e26ca9d823
Source dataset
uspto-grants-2001_05
Patent number
US06229055B1

Reaction notes

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