Lithium Hydroxide → 4-{3-Chloro-4-[3,3,3-trifluoro-2-hydroxy-1-methyl-2-(2-methyl-pyridin-4-yl)-propyl]-phenoxymethyl}-benzoic acid

4-{3-Chloro-4-[3,3,3-trifluoro-2-hydroxy-1-methyl-2-(2-methyl-pyridin-4-yl)-propyl]-phenoxymethyl}-benzoic acid ethyl ester (250 mg) was dissolved in THF/methanol=5/1 (6 mL) followed by the addition of aqueous LiOH solution (1.0M, 0.54 mL). The mixture was heated to 50° C. for 3.5 hours. The reaction was cooled and concentrated in vacuo. The residue was dissolved in water (5 mL) and aqueous HCl solution (1.0M, 0.54 mL) was added. The mixture was stirred at r.t. for 15 minutes and then at 0° C. for 1 hour. The resulting precipitate was filtered off and washed with cold water. The residual water was removed by co-evaporation with toluene. The resulting solid was dried in vacuo. The title compound was obtained as a colorless solid (220 mg, 93%). MS (m/e)=480.1 [MH+].

1. temperatureThe reaction was cooled
2. concentrationconcentrated in vacuo
3. dissolutionThe residue was dissolved in water (5 mL)
4. additionaqueous HCl solution (1.0M, 0.54 mL) was added
5. waitat 0° C. for 1 hour
6. filtrationThe resulting precipitate was filtered off
7. washwashed with cold water
8. customThe residual water was removed by co-evaporation with toluene
9. customThe resulting solid was dried in vacuo

ORD record

ord-3f4698f6137f446a9b1952a18c949c04

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08138189B2