Hydrochloric Acid → HCID 68870795, compound

HRID 2224892Notes

Reaction equation

HRID 2224892 reaction equation
[CH:1]1([CH2:7][C:8]2([CH3:25])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]([OH:18])=[C:10](C(OCC)=O)[C:9]2=[O:24])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl>O1CCOCC1>[CH:1]1([CH2:7][C:8]2([CH3:25])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]([OH:18])=[CH:10][C:9]2=[O:24])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68872804HCID 68872804, compound

Product 1

HCID 68870795HCID 68870795, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
25 °C

Procedure

A solution of Example 41D (4.56 g, 13.3 mmol) in 1,4-dioxane (30 mL) was treated with aqueous 1N hydrochloric acid solution (30 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 (2.72 g, 76%). 1H NMR (300 MHz, CDCl3): δ ppm 0.85 m, 6 H) 1.43 m, 8 H) 2.03 m, 2 H) 3.80 m, 1 H) 6.05 m, 0.5 H) 7.51 m, 3 H) 8.06 (m, 0.5H) 8.13 m, 0.5 H). MS (ESI−) m/z 269 (M−H)−.

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-a13d591b62ac44dcae2e9708676a134b
Source dataset
uspto-grants-2008_05
Patent number
US07378414B2

Reaction notes

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