Hydrochloric Acid → HCID 22221609, compound

HRID 1836044Notes

Reaction equation

HRID 1836044 reaction equation
CO[C:3]1[CH:8]=[CH:7][C:6]([O:9]C)=[CH:5][C:4]=1[CH2:11][C:12]([C:14]1[CH:19]=[CH:18][C:17]([O:20]C)=[C:16]([F:22])[CH:15]=1)=[O:13].Cl>>[F:22][C:16]1[CH:15]=[C:14]([C:12]2[O:13][C:3]3[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][C:4]=3[CH:11]=2)[CH:19]=[CH:18][C:17]=1[OH:20]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 22221620HCID 22221620, compound

Product 1

HCID 22221609HCID 22221609, compound

Procedure

The ketone 125 (1 g, 3.3 mmol) was heated with pyr-HCl at 180-200° C. until TLC indicated reaction completion. The reaction was worked up by partitioning between 2 N HCl aq and EtOAc and washing the EtOAc with saturated NaHCO3, brine, and drying over MgSO4. The solution was filtered, concentrated and chromatographed on silica gel to yield 0.48 g of impure pdt. The product thus obtained was recrystallized from EtOAc/hexanes to yield desired product plus a small amt of unidentified impurity: Mp=218-222° C.; 1H NMR (DMSO-d6) δ 10.39 (s, 1 H), 9.20 (s, 1 H), 7.74 (t, 1 H, J=8.7 Hz), 7.37 (d, 1 H, J=8.8 Hz), 6.96-6.94 (m, 2 H), 6.79-6.70 (m, 3 H); MS 243 (M−H)−

Workup

  1. customreaction completion
  2. customby partitioning between 2 N HCl aq and EtOAc
  3. washwashing the EtOAc with saturated NaHCO3, brine
  4. dry with materialdrying over MgSO4
  5. filtrationThe solution was filtered
  6. concentrationconcentrated
  7. customchromatographed on silica gel
  8. customto yield 0.48 g of impure pdt
  9. customThe product thus obtained
  10. customwas recrystallized from EtOAc/hexanes

Sources & evidence

ORD record
ord-b5fdb201ba114e3aacd301381444cc3f
Source dataset
uspto-grants-2004_08
Patent number
US06774248B2

Reaction notes

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