Hydrochloric Acid → HCID 22467920, compound

HRID 1935237Notes

Reaction equation

C([O:3][C:4](=[O:26])[CH:5]([C:12]1[CH:17]=[CH:16][C:15]([S:18]([CH:21]2[CH2:25][CH2:24][CH2:23][CH2:22]2)(=[O:20])=[O:19])=[CH:14][CH:13]=1)[CH2:6][CH:7]1[CH2:11][CH2:10][CH2:9][CH2:8]1)C.[OH-].[Li+].Cl>O1CCCC1.O.CO.C(Cl)(Cl)Cl.O>[CH:21]1([S:18]([C:15]2[CH:14]=[CH:13][C:12]([CH:5]([CH2:6][CH:7]3[CH2:8][CH2:9][CH2:10][CH2:11]3)[C:4]([OH:26])=[O:3])=[CH:17][CH:16]=2)(=[O:19])=[O:20])[CH2:22][CH2:23][CH2:24][CH2:25]1

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of 2-(4-cyclopentanesulfonyl-phenyl)-3-cyclopentyl-propionic acid ethyl ester (160 mg, 0.42 mmol) in tetrahydrofuran/water/methanol (1.05 mL, 3:1:1) was treated with a 1N aqueous lithium hydroxide solution (0.85 mL, 0.85 mmol). The reaction was stirred at 25° C. for 18 h. At this time, the reaction was diluted with chloroform (30 mL) and water (50 mL), acidified to pH=1 with a 1N aqueous hydrochloric acid solution, and extracted with a solution of chloroform/methanol (90/10, 3×50 mL). The combined organic extracts were dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 90/10 chloroform/methanol) afforded 2-(4-cyclopentanesulfonyl-phenyl)-3-cyclopentyl-propionic acid (101.9 mg, 68.7%) as an off white solid: mp 165-167° C.; FAB-HRMS m/e calcd for C19H26O4S (M+H)+ 351.1630 found 351.1646.

Workup

extractionextracted with a solution of chloroform/methanol (90/10, 3×50 mL)
dry with materialThe combined organic extracts were dried over sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-5e80a52495474de2983ce46c02b67399
Source dataset: uspto-grants-2002_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06384220B2

Reaction notes

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