Acetic Acid → (3-{3-[(2-Chloro-3-trifluoromethyl-benzyl)-(2-thiophen-2-yl-propyl)-amino]-propoxy}-phenyl)-acetic acid hydrochloride salt

A solution of (3-{3-[(2-chloro-3-trifluoromethyl-benzyl)-(2-thiophen-2-yl-propyl)-amino]-propoxy}-phenyl)-acetic acid methyl ester (25 mg, 0.05 mmol) in THF (9 ml) and water (6 ml) was treated with aqueous LiOH (1.0 N, 0.29 ml, 1.0 mmol). After stirring at room temperature for 2 h, additional LiOH (0.29 ml, 1.0 mmol) was added and stirring was continued for 2 h. The reaction was neutralized with AcOH and poured into water and ethyl acetate. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic layers were washed with brine, dried over sodium sulfate and concentrated in vacco. The crude mixture was purified by HPLC to give the free amine of title compound as an oil (15 mg, 58%). MS m/e 520.2 (M+H)+. To a solution of the free amine in diethyl ether was added HCl in diethyl ether (1.0M) to precipitate HCl salt The suspension was filtered and dried to give the title compound as a white solid.

1. stirringstirring
2. waitwas continued for 2 h
3. customThe layers were separated
4. extractionthe aqueous layer was extracted with EtOAc
5. washThe combined organic layers were washed with brine
6. dry with materialdried over sodium sulfate
7. concentrationconcentrated in vacco
8. customThe crude mixture was purified by HPLC

ORD record

ord-5cce173a04f64fe79288567cca996507

Source dataset

uspto-grants-2008_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07365085B2