Hydrochloric Acid → HCID 69268966, compound

HRID 494477Notes

Reaction equation

HRID 494477 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH2:25][CH2:26][CH3:27])([CH2:22][CH2:23][CH3:24])[C:9]([CH:11](C(OCC)=O)[C:12]([O:14]CC)=O)=[O:10])=[CH:4][CH:3]=1.ClCCl.Cl>CS(O)(=O)=O.O1CCCC1.O>[F:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:6][CH:7]=1)[C:8]([CH2:22][CH2:23][CH3:24])([CH2:25][CH2:26][CH3:27])[C:9](=[O:10])[CH:11]=[C:12]2[OH:14]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 68874303HCID 68874303, compound

Product 1

HCID 69268966HCID 69268966, compoundYield 70%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6395Methanesulfonic AcidSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

The compound of Example 14F (6.0 g, 15.75 mmol) was dissolved in methanesulfonic acid (35 mL) and warmed at 50° C. for 5 h. The mixture was cooled and added to a mixture of ice and dichloromethane, followed by stirring until all ice had melted. The layers were separated and the aqueous phase was extracted again with dichloromethane. The combined organic layers were dried (Na2SO4) and concentrated in vacuo to afford an amber oil, which was dissolved in tetrahydrofuran (60 mL) and warmed at reflux with 1 N HCl solution (50 mL) for 18 h. The mixture was cooled and diluted with water and extracted with ethyl acetate. The organic layer was extracted with water and saturated NaCl solution. Drying (Na2SO4) and concentration in vacuo afforded a brown solid, which was triturated with ether-hexane and collected by filtration. These procedures afforded the title compound (2.89 g, 70%) as an off-white solid. 1H NMR (300 MHz, DMSO-d6): δ 0.51 (m, 2 H) 0.64 (m, 6 H) 0.84 (m, 2 H) 1.84 (m, 2 H) 1.99 (m, 2 H) 5.80 (s, 1 H) 7.43 (m, 1 H) 7.57 (dd, J=9.56, 2.57 Hz, 1 H) 7.67 (d, J=5.52 Hz, 1 H) 11.75 (s, 1 H).

Workup

  1. temperatureThe mixture was cooled
  2. customThe layers were separated
  3. extractionthe aqueous phase was extracted again with dichloromethane
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customto afford an amber oil, which
  7. temperaturewarmed
  8. temperatureThe mixture was cooled
  9. extractionextracted with ethyl acetate
  10. extractionThe organic layer was extracted with water and saturated NaCl solution
  11. customDrying
  12. concentration(Na2SO4) and concentration in vacuo
  13. customafforded a brown solid, which
  14. customwas triturated with ether-hexane
  15. filtrationcollected by filtration

Sources & evidence

ORD record
ord-33a50466db594c818fca58eee2e4a084
Source dataset
uspto-grants-2009_05
Patent number
US07538105B2

Reaction notes

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