Hydrochloric Acid → HCID 59570902, compound

HRID 2192897Notes

Reaction equation

HRID 2192897 reaction equation
[CH:1]1([C:4]2[CH:5]=[C:6]([C:16](=[CH:22][C@@H:23]3[CH2:43][CH2:42][C:25]4(O[C@@H](C5C=CC=CC=5)[C@H](C5C=CC=CC=5)[O:26]4)[CH2:24]3)[C:17]([O:19]CC)=[O:18])[CH:7]=[CH:8][C:9]=2[S:10]([CH:13]2[CH2:15][CH2:14]2)(=[O:12])=[O:11])[CH2:3][CH2:2]1.[OH-].[K+].Cl.C(Cl)(Cl)Cl>CO.O1CCOCC1>[CH:1]1([C:4]2[CH:5]=[C:6](/[C:16](=[CH:22]\[C@@H:23]3[CH2:43][CH2:42][C:25](=[O:26])[CH2:24]3)/[C:17]([OH:19])=[O:18])[CH:7]=[CH:8][C:9]=2[S:10]([CH:13]2[CH2:14][CH2:15]2)(=[O:12])=[O:11])[CH2:2][CH2:3]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6212ChloroformHCID 14797Potassium HydroxideHCID 68671825HCID 68671825, compound

Product 1

HCID 59570902HCID 59570902, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

Ethyl 2-[3-cyclopropyl-4-(cyclopropylsulfonyl)phenyl]-3-[(2S,3S,7R)-2,3-diphenyl-1,4-dioxaspiro[4.4]non-7-yl]acrylate (1.77 g, (E), (Z) mixture) was dissolved in a mixed solvent of methanol (21.2 mL) and dioxane (21.2 mL), and to this solution was slowly added 8 M aqueous potassium hydroxide solution (21.2 mL), which had been separately prepared. It was stirred at room temperature for 10 minutes, and then stirred in an oil bath at 70° C. for 2 hours under heating. It was left to be cooled to room temperature, and hydrochloric acid was carefully added thereto under ice-cooling. The mixture was stirred for 2 hours under heating in an oil bath at 90° C., and cooled to room temperature again. Chloroform was added thereto and the organic layer was separated. The aqueous layer was extracted with chloroform, combined with the organic layer, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain (2E)-2-[3-cyclopropyl-4-(cyclopropylsulfonyl)phenyl]-3-[(1R)-3-oxocyclopentyl]acrylic acid (952 mg).

Workup

  1. customhad been separately prepared
  2. stirringstirred in an oil bath at 70° C. for 2 hours
  3. temperatureunder heating
  4. waitIt was left
  5. temperatureto be cooled to room temperature
  6. temperatureunder ice-cooling
  7. stirringThe mixture was stirred for 2 hours
  8. temperatureunder heating in an oil bath at 90° C.
  9. temperaturecooled to room temperature again
  10. customthe organic layer was separated
  11. extractionThe aqueous layer was extracted with chloroform
  12. dry with materialdried over anhydrous sodium sulfate
  13. concentrationconcentrated under reduced pressure
  14. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-66d1823b841b4c83b2de3e16b8f65108
Source dataset
uspto-grants-2012_12
Patent number
US08329707B2

Reaction notes

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