Hydrochloric Acid → 2-(3-Chloro-4-methylsulfanyl-phenyl)-3-cyclopentyl-propionic acid
Reaction equation
C([O:3][C:4](=[O:21])[CH:5]([C:12]1[CH:17]=[CH:16][C:15]([S:18][CH3:19])=[C:14]([Cl:20])[CH:13]=1)[CH2:6][CH:7]1[CH2:11][CH2:10][CH2:9][CH2:8]1)C.[OH-].[K+].Cl>C(O)C>[Cl:20][C:14]1[CH:13]=[C:12]([CH:5]([CH2:6][CH:7]2[CH2:11][CH2:10][CH2:9][CH2:8]2)[C:4]([OH:21])=[O:3])[CH:17]=[CH:16][C:15]=1[S:18][CH3:19]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
A solution of 2-(3-chloro-4-methylsulfanyl-phenyl)-3-cyclopentyl-propionic acid ethyl ester (0.45 g, 1.39 mmol) in ethanol (3 mL) was treated with a 10% aqueous potassium hydroxide solution (2 mL). The reaction mixture was stirred under nitrogen at 25° C. for 16 h. The reaction mixture was then acidified with a 1N aqueous hydrochloric acid solution (5 mL). The reaction mixture was then extracted with methylene chloride (3×15 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo to afford 2-(3-chloro-4-methylsulfanyl-phenyl)-3-cyclopentyl-propionic acid (0.29 g, 70%) as a white solid: EI-HRMS m/e calcd for C15H19ClO2S (M+) 298.0794, found 298.0798.
Workup
- extractionThe reaction mixture was then extracted with methylene chloride (3×15 mL)
- dry with materialThe combined organic layers were dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-ab8677b73cc94d139c7647784a607b5a
- Source dataset
- uspto-grants-2007_05
- Patent number
- US07223868B2
Reaction notes
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