Hydrochloric Acid → HCID 25259744, compound

HRID 494564Notes

Reaction equation

HRID 494564 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C@:5]([CH3:17])([CH2:12][CH2:13][CH:14]([CH3:16])[CH3:15])[C:4](=[O:18])[C:3]=1C(OCC)=O.Cl>O1CCOCC1>[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C@:5]([CH3:17])([CH2:12][CH2:13][CH:14]([CH3:15])[CH3:16])[C:4](=[O:18])[CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 54740022HCID 54740022, compound

Product 1

HCID 25259744HCID 25259744, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
25 °C

Procedure

A solution of Example 40D (2.60, 8.22 mmol) in 1,4-dioxane (25 mL) was treated with aqueous 1N hydrochloric acid solution (25 mL) and refluxed for 3 hours. The mixture was cooled to 25° C. and partitioned between ethyl acetate and water. The ethyl acetate layer was washed with water and brine, dried with sodium sulfate, filtered, and concentrated in vacuo. The residue was triturated in hot hexane and filtered. The precipitate was dried to give the title compound (1.60 g, 80%). 1H NMR (300 MHz, CDCl3): δ ppm 0.44 (m, 0.5H) 0.73 (m, 3.5H) 0.80 (m, 3H) 1.06 (m, 1H) 1.39 (m, 1H) 1.56 (s, 1.5H) 1.59 (s, 1.5H) 2.04 (m, 1H) 2.30 (m, 1H) 3.74 (s, 0.5H) 3.75 (s, 0.5H) 6.63 (s, 0.5H) 7.46 (m, 2H) 7.66 (m, 1H) 8.08 (m, 0.5H) 8.20 (m, 0.5H).

Workup

  1. temperaturerefluxed for 3 hours
  2. custompartitioned between ethyl acetate and water
  3. washThe ethyl acetate layer was washed with water and brine
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was triturated in hot hexane
  8. filtrationfiltered
  9. customThe precipitate was dried

Sources & evidence

ORD record
ord-07f44677c9694e588fd5a805ff8297bb
Source dataset
uspto-grants-2009_05
Patent number
US07538105B2

Reaction notes

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