Sodium Hydroxide → HCID 21958963, compound

Temperature

25 °C

A solution of 2-(3-chloro-4-methanesulfonyl-phenyl)-3-(3-oxo-cyclopentyl)-propionic acid methyl ester (1.02 g, 2.84 mmol) in methanol (7.1 mL) was treated with a 1N aqueous sodium hydroxide solution (6.0 μL, 6.0 mmol). The reaction mixture was stirred at 25° C. for 16 h. The reaction mixture was then concentrated in vacuo to remove methanol. The resulting aqueous residue was diluted with water (100 mL) and acidified to pH=3 with a 1N aqueous hydrochloric acid solution then extracted with ethyl acetate (2×150 mL). The combined organic layers were washed with a saturated aqueous sodium chloride solution (100 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. The resulting yellow oily solid was triturated with ethyl acetate/petroleum ether to afford 2-(3-chloro-4-methanesulfonyl-phenyl)-3-(3-oxo-cyclopentyl)-propionic acid (800.0 mg, 82%) as a white solid: mp 164-167° C.; (ES)+-HRMS m/e calcd for C15H17ClO5S (M+H)+ 345.0558. found 345.0561.

1. concentrationThe reaction mixture was then concentrated in vacuo
2. customto remove methanol
3. additionThe resulting aqueous residue was diluted with water (100 mL)
4. extractionthen extracted with ethyl acetate (2×150 mL)
5. washThe combined organic layers were washed with a saturated aqueous sodium chloride solution (100 mL)
6. dry with materialdried over sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customThe resulting yellow oily solid was triturated with ethyl acetate/petroleum ether

ORD record

ord-ce7cf1d61adc4c48bedc202f8b0bddfb

Source dataset

uspto-grants-2007_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07259166B2