Hydrochloric Acid → HCID 57604660, compound

HRID 2224838Notes

Reaction equation

HRID 2224838 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 57604823HCID 57604823, compound

Product 1

HCID 57604660HCID 57604660, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
25 °C

Procedure

A solution of Example 28D (2.06 g, 6.52 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 (1.05 g, 66%). 1H NMR (300 MHz, CDCl3) δ ppm 0.44 (m, 0.5 H) 0.73 (m, 3.5 H) 0.80 (m, 3 H) 1.06 (m, 1 H) 1.39 (m, 1 H) 1.56 (s, 1.5 H) 1.59 (s, 1.5 H) 2.04 (m, 1 H) 2.30 (m, 1 H) 3.74 (s, 0.5 H) 3.75 (s, 0.5 H) 6.63 (s, 0.5 H) 7.46 (m, 2 H) 7.66 (m, 1 H) 8.08 (m, 0.5 H) 8.20 (m, 0.5 H). MS (DCI NH3+) m/z 262 (M+NH4)+.

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-212ed8a686874746b6ef3f2c11c3ae4c
Source dataset
uspto-grants-2008_05
Patent number
US07378414B2

Reaction notes

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