Potassium Hydroxide → 2-(3-Chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionic acid

HRID 398689Notes

Reaction equation

HRID 398689 reaction equation
C[O:2][C:3](=[O:22])[CH:4]([C:11]1[CH:16]=[CH:15][C:14]([S:17]([CH3:20])(=[O:19])=[O:18])=[C:13]([Cl:21])[CH:12]=1)[CH2:5][CH:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1.C(OC(=O)C(C1C=CC(S(C)(=O)=O)=C(Cl)C=1)CC1CCCC1)C.[OH-].[K+]>C(O)C.O>[Cl:21][C:13]1[CH:12]=[C:11]([CH:4]([CH2:5][CH:6]2[CH2:10][CH2:9][CH2:8][CH2:7]2)[C:3]([OH:22])=[O:2])[CH:16]=[CH:15][C:14]=1[S:17]([CH3:20])(=[O:19])=[O:18]

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 53763168HCID 53763168, compoundHCID 54447124HCID 54447124, compound

Product 1

HCID 120676542-(3-Chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionic acidYield 82%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

The mixture of 2-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionic acid methyl ester and 2-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionic acid ethyl ester (937 mg) was dissolved in ethanol (30 mL). This solution was then treated with a solution of potassium hydroxide (733 mg, 13.1 mmol) in water (7 mL). The resulting yellow solution was stirred at 25° C. for 3 h and then concentrated in vacuo to remove ethanol. The aqueous residue was treated with a 1N aqueous hydrochloric acid solution until the pH=2. The product was then extracted into methylene chloride (3×15 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 75/25 hexanes/ethyl acetate plus 1% acetic acid) afforded 2-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionic acid (787 mg, 82% for two steps) as a white solid: mp 123.9-126.2° C.; FAB-HRMS m/e calcd for C15H19ClO4S (M+H)+ 331.0771, found 331.0776.

Workup

  1. concentrationconcentrated in vacuo
  2. customto remove ethanol
  3. additionThe aqueous residue was treated with a 1N aqueous hydrochloric acid solution until the pH=2
  4. extractionThe product was then extracted into methylene chloride (3×15 mL)
  5. dry with materialThe combined organic layers were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-db805001d5ff47628e83ee94bc22c365
Source dataset
uspto-grants-2003_08
Patent number
US06610846B1

Reaction notes

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