Hydrochloric Acid → 3-(2-Methyl-4-{1-[4-methyl-2-(4-trifluoromethyl-phenyl)-oxazol-5-yl]-ethoxy}-phenyl)-propionic acid

HRID 860666Notes

Reaction equation

C[O:2][C:3](=[O:32])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH:13]([C:15]2[O:19][C:18]([C:20]3[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=3)=[N:17][C:16]=2[CH3:30])[CH3:14])=[CH:8][C:7]=1[CH3:31].CO.[OH-].[Li+].Cl>C1COCC1.O>[CH3:31][C:7]1[CH:8]=[C:9]([O:12][CH:13]([C:15]2[O:19][C:18]([C:20]3[CH:21]=[CH:22][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:24][CH:25]=3)=[N:17][C:16]=2[CH3:30])[CH3:14])[CH:10]=[CH:11][C:6]=1[CH2:5][CH2:4][C:3]([OH:32])=[O:2]

Participants

Conditions

Temperature: 60 °C

Procedure

3-(2-Methyl-4-{1-[4-methyl-2-(4-trifluoromethyl-phenyl)-oxazol-5-yl]-ethoxy}-phenyl)-propionic acid methyl ester (0.176 g, 0.393 mmol) is dissolved in 20 mL of a 3:2:1 mixture of THF:MeOH:H2O. Lithium hydroxide (0.050 g, 2.08 mmol) is added and the resulting mixture is heated to 60° C. for 1 hr. The mixture is cooled to room temperature, diluted with 50 mL water and the pH is adjusted to 2–3 with 1M HCl. The product is extracted with two 50 mL portions of ethyl acetate. The combined organic extracts are washed with 50 mL water, dried over anhydrous magnesium sulfate, filtered, and concentrated to yield the title compound, 3-(2-Methyl-4-{1-[4-methyl-2-(4-trifluoromethyl-phenyl)-oxazol-5-yl]-ethoxy}-phenyl)-propionic acid as a white solid, 0.12 g (71%). MS (M++1) 434.

Workup

temperatureThe mixture is cooled to room temperature
extractionThe product is extracted with two 50 mL portions of ethyl acetate
washThe combined organic extracts are washed with 50 mL water
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-ac68e75fe27a40ecb79665f41b4f9851
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07153878B2

Reaction notes

Loading…