Hydrochloric Acid → 2-Methyl-3-{5-[3-(5-methyl-2-phenyl-oxazol-4-yl)-propyl]-thiophen-2-yl}-2-phenoxy-propionic Acid

HRID 585275Notes

Reaction equation

C[O:2][C:3](=[O:34])[C:4]([CH3:33])([O:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH2:5][C:6]1[S:7][C:8]([CH2:11][CH2:12][CH2:13][C:14]2[N:15]=[C:16]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[O:17][C:18]=2[CH3:19])=[CH:9][CH:10]=1.[OH-].[Na+].Cl>CCO.O>[CH3:33][C:4]([O:26][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)([CH2:5][C:6]1[S:7][C:8]([CH2:11][CH2:12][CH2:13][C:14]2[N:15]=[C:16]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[O:17][C:18]=2[CH3:19])=[CH:9][CH:10]=1)[C:3]([OH:34])=[O:2]

Participants

Conditions

Temperature: 60 °C

Procedure

2-Methyl-3-{5-[3-(5-methyl-2-phenyl-oxazol-4-yl)-propyl]-thiophen-2-yl}-2-phenoxy-propionic acid methyl ester 400 mg) was dissolved in EtOH (10 mL), and then 5 N NaOH (3 mL) was added. This mixture was allowed to stir at 60° C. for 1 h. The mixture was cooled to room temperature and then acidified to pH=2 by the dropwise addition of 5 N HCl. This acidic mixture was diluted with H2O (10 mL) and then extracted with CH2Cl2 (2×25 mL). The organic layers were combined, dried over NaCl, and solvent removed in vacuo which provided 354 mg (92%) of desired acid: 1H NMR (400 MHz, CDCl3) δ 8.05 (d, 2H), 7.39 (m, 4H), 7.23 (m, 1H), 7.03 (t, 1H), 6.95 (d, 2H), 6.70 (d, 1H), 6.62 (d, 1H), 3.40 (d, 1H), 3.30 (d, 1H), 2.80 (t, 2H), 2.52 (t, 2H), 2.27 (s, 3H), 2.02 (m, 2H), 1.44 (s, 3H); MS (EI) 462.2 (M+H)+.

Workup

temperatureThe mixture was cooled to room temperature
extractionextracted with CH2Cl2 (2×25 mL)
dry with materialdried over NaCl, and solvent
customremoved in vacuo which

Sources & evidence

ORD record: ord-f5d0e5820461432cbecb3277e81918f9
Source dataset: uspto-grants-2005_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06930120B2

Reaction notes

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