Hydrochloric Acid → HCID 59331463, compound

HRID 1881819Notes

Reaction equation

HRID 1881819 reaction equation
[CH:1]1([CH2:6][CH:7]([C:12]2[CH:17]=[CH:16][C:15]([S:18]([CH:21]3[CH2:23][CH2:22]3)(=[O:20])=[O:19])=[CH:14][CH:13]=2)[C:8]([O:10]C)=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.O1CCCC1.[OH-].[Na+].Cl>CO>[CH:1]1([CH2:6][CH:7]([C:12]2[CH:17]=[CH:16][C:15]([S:18]([CH:21]3[CH2:23][CH2:22]3)(=[O:19])=[O:20])=[CH:14][CH:13]=2)[C:8]([OH:10])=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 59331551HCID 59331551, compound

Product 1

HCID 59331463HCID 59331463, compoundYield 89.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of methyl 3-cyclopentyl-2-[4-(cyclopropylsulfonyl)phenyl]propanoate (1.95 g) in a mixed solvent of tetrahydrofuran (40 mL) and methanol (20 mL) was added 2N aqueous sodium hydroxide solution (10 mL), and the mixture was stirred at 50° C. for 3 hr. The reaction mixture was acidified with 1N hydrochloric acid, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was recrystallized from hexane-diethyl ether to give the title compound (1.67 g, 89%) as colorless crystals. MS: 323 (MH+).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was recrystallized from hexane-diethyl ether

Sources & evidence

ORD record
ord-b9086844c9c844a1b47e55100375c157
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

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