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

HRID 430322Notes

Reaction equation

HRID 430322 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, from above, (937 mg) was dissolved in ethanol (30 mL) and allowed to dissolve. To this solution was then added a solution of potassium hydroxide (733 mg, 13.1 mmol) in water (7 mL). The yellow solution was then stirred for 3 h at 25° C. It was concentrated in vacuo to remove the ethanol and then IN hydrochloric acid was added until the pH=2. This was then extracted with methylene chloride (3×15 mL). The organic layers were then 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% over two steps) as a white solid: mp: 123.9-126.2° C.; FAB-HRMS m/e calcd for C15H19O4SCl (M+H)+331.0771, found 331.0776.

Workup

  1. dissolutionto dissolve
  2. concentrationIt was concentrated in vacuo
  3. customto remove the ethanol
  4. additionIN hydrochloric acid was added until the pH=2
  5. extractionThis was then extracted with methylene chloride (3×15 mL)
  6. dry with materialThe organic layers were then dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1d9d991c8eb7479284aed2f384f83964
Source dataset
uspto-grants-2001_11
Patent number
US06320050B1

Reaction notes

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