Hydrochloric Acid → HCID 69268023, compound

HRID 494545Notes

Reaction equation

HRID 494545 reaction equation
[CH:1]1([CH2:7][CH2:8][CH2:9][C:10]2([CH3:27])[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]([OH:20])=[C:12](C(OCC)=O)[C:11]2=[O:26])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl>O1CCOCC1>[CH:1]1([CH2:7][CH2:8][CH2:9][C:10]2([CH3:27])[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]([OH:20])=[CH:12][C:11]2=[O:26])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68873381HCID 68873381, compound

Product 1

HCID 69268023HCID 69268023, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
25 °C

Procedure

A solution of Example 36F (2.14 g, 5.78 mmol) in 1,4-dioxane (20 mL) was treated with aqueous 1N hydrochloric acid solution (20 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 (0.513 g, 30%).

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-5bceb2f858714271b2fe73c1417c5bd1
Source dataset
uspto-grants-2009_05
Patent number
US07538105B2

Reaction notes

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