Lithium Hydroxide → 3-Cyclopentyl-2-(3-nitro-phenyl)-propionic acid

Temperature

25 °C

A solution of 3-cyclopentyl-2-(3-nitro-phenyl)-propionic acid methyl ester (0.55 g, 2.0 mmol) in tetrahydrofuran/water (12 mL, 3:1) was treated with lithium hydroxide (185 mg, 4.40 mmol). The reaction was stirred at 25° C. for 48 h. The tetrahydrofuran was then removed in vacuo. The residue was diluted with water (25 mL) and extracted with ether (1×20 mL). The aqueous layer was acidified to pH=2 with a 3N aqueous hydrochloric acid solution. The solution was extracted with methylene chloride (3×25 mL). The combined organic layers were washed with a saturated aqueous sodium chloride solution (2×25 mL), dried over sodium sulfate, filtered, and concentrated in vacuo to give 3-cyclopentyl-2-(3-nitro-phenyl)-propionic acid (0.48 g, 91.9%) as a tan solid: mp 95-99° C.; EI-HRMS m/e calcd for C14H17NO4 (M+) 263.1157, found 263.1156.

1. customThe tetrahydrofuran was then removed in vacuo
2. additionThe residue was diluted with water (25 mL)
3. extractionextracted with ether (1×20 mL)
4. extractionThe solution was extracted with methylene chloride (3×25 mL)
5. washThe combined organic layers were washed with a saturated aqueous sodium chloride solution (2×25 mL)
6. dry with materialdried over sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated in vacuo

ORD record

ord-1c6005dcfbd5429dbf837bacb48cab2b

Source dataset

uspto-grants-2003_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06610846B1