Ammonium Chloride → 5-Chloro-2-(4-chloro-2-trifluoromethylphenyl)pentanoic acid amide

Ammonium chloride (3.23 g), 1-hydroxybenzotriazole (2.45 g), IPEA (13.7 mL) and benzotriazol-1-yloxytris(pyrrolidino)phosphonimn hexafluorophosphate (9.43 g) were sequentially added to a solution of 5-chloro-2-(4-chloro-2-trifluoromethylphenyl)pentanoic acid (4.75 g) in N,N-dimethylformamide (45 mL). The mixture was stirred at room temperature overnight. Ice water and tert-butyl methyl ether were added to the reaction solution, and the organic layer was separated. The aqueous layer was reextracted with tert-butyl methyl ether. The combined organic layers were sequentially washed with 1 N hydrochloric acid, water, a saturated sodium bicarbonate aqueous solution and brine, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (carrier: Wakogel™ C-200; elution solvent:heptane:ethyl acetate=4:1→3:1) to obtain 3.89 g of the title compound. The property values of the compound are as follows.

1. customthe organic layer was separated
2. washThe combined organic layers were sequentially washed with 1 N hydrochloric acid, water
3. dry with materiala saturated sodium bicarbonate aqueous solution and brine, dried over anhydrous magnesium sulfate
4. concentrationconcentrated under reduced pressure
5. customThe resulting residue was purified by silica gel column chromatography (carrier: Wakogel™ C-200; elution solvent:heptane:ethyl acetate=4:1→3:1)

ORD record

ord-fbfe26304c564830855536f9b2561f3e

Source dataset

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08754100B2