Lithium Hydroxide → 2-(4-Chloro-3-nitro-phenyl)-3-cyclopentyl-propionic acid

Temperature

25 °C

A solution of 2-(4-chloro-3-nitro-phenyl)-3-cyclopentyl-propionic acid methyl ester (260 mg, 0.834 mmol) in tetrahydrofuran (3 mL) was treated with a 0.8M aqueous lithium hydroxide solution (1.25 mL, 1.00 mmol). The reaction mixture was stirred at 25° C. for 15 h. The resulting reaction mixture was partitioned between water (50 mL) and ethyl acetate (50 mL) and then treated with a 1N aqueous hydrochloric acid solution (10 mL). The layers were shaken and separated. The aqueous layer was further extracted with ethyl acetate (50 mL). The combined organic layers were dried over magnesium sulfate, filtered, and concentrated in vacuo to afford 2-(4-chloro-3-nitro-phenyl)-3-cyclopentyl-propionic acid (243 mg, 98%) as a yellow solid which was used without further purification: mp 112–115° C.; FAB-HRMS m/e calcd for C14H16ClNO4 (M+H)+ 298.0847, found 298.0851.

1. customThe resulting reaction mixture
2. customwas partitioned between water (50 mL) and ethyl acetate (50 mL)
3. additiontreated with a 1N aqueous hydrochloric acid solution (10 mL)
4. stirringThe layers were shaken
5. customseparated
6. extractionThe aqueous layer was further extracted with ethyl acetate (50 mL)
7. dry with materialThe combined organic layers were dried over magnesium sulfate
8. filtrationfiltered
9. concentrationconcentrated in vacuo

ORD record

ord-7f6ec31fa1b14db99bb2053d05c61cd9

Source dataset

uspto-grants-2007_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07223868B2