Hydrochloric Acid → (2R)-2-[3-cyclopropyl-4-(cyclopropylsulfonyl)phenyl]-3-[(1R)-3-oxocyclopentyl]propanoic acid

HRID 2192910Notes

Reaction equation

HRID 2192910 reaction equation
[CH:1]1([C:4]2[CH:5]=[C:6]([C@@H:16]([CH2:20][C@H:21]3[CH2:25][CH2:24][C:23]4(OCC(C)(C)C[O:26]4)[CH2:22]3)[C:17]([OH:19])=[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.Cl>CC(C)=O>[CH:1]1([C:4]2[CH:5]=[C:6]([C@@H:16]([CH2:20][C@H:21]3[CH2:25][CH2:24][C:23](=[O:26])[CH2:22]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

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59570883(2R)-2-[3-cyclopropyl-4-(cyclopropylsulfonyl)phenyl]-3-[(2R)-8,8-dimethyl-6,10-dioxaspiro[4.5]dec-2-yl]propionic acid

Product 1

HCID 59570882(2R)-2-[3-cyclopropyl-4-(cyclopropylsulfonyl)phenyl]-3-[(1R)-3-oxocyclopentyl]propanoic acidYield 100%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of (2R)-2-[3-cyclopropyl-4-(cyclopropylsulfonyl)phenyl]-3-[(2R)-8,8-dimethyl-6,10-dioxaspiro[4.5]dec-2-yl]propionic acid (22 g), 4 M hydrochloric acid (22 mL), and acetone (88 mL) was stirred under heating and reflux for 2 hours. The solvent was evaporated under reduced pressure, and then to the residue were added ethyl acetate/water (1/3, 300 mL) and sodium hydroxide (5.7 g) under ice-cooling. To the aqueous layer was added concentrated hydrochloric acid under ice-cooling to adjust the pH to 1, and chloroform was added thereto. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate, and the solvent was then evaporated under reduced pressure to obtain (2R)-2-[3-cyclopropyl-4-(cyclopropylsulfonyl)phenyl]-3-[(1R)-3-oxocyclopentyl]propionic acid (17.9 g) as a colorless amorphous substance.

Workup

  1. temperatureunder heating
  2. temperaturereflux for 2 hours
  3. customThe solvent was evaporated under reduced pressure
  4. additionto the residue were added ethyl acetate/water (1/3, 300 mL) and sodium hydroxide (5.7 g) under ice-
  5. temperaturecooling
  6. additionTo the aqueous layer was added concentrated hydrochloric acid under ice-
  7. temperaturecooling
  8. additionwas added
  9. washThe organic layer was washed with saturated brine
  10. dry with materialdried over anhydrous sodium sulfate
  11. customthe solvent was then evaporated under reduced pressure

Sources & evidence

ORD record
ord-967753dac5dd464e87dceec43f930c7a
Source dataset
uspto-grants-2012_12
Patent number
US08329707B2

Reaction notes

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