Sodium Hydroxide → 2-Methyl-2-[2-methyl-4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]phenoxy]propanoic acid

HRID 1609947Notes

Reaction equation

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

Participants

Conditions

Temperature: 55 °C

Procedure

A solution of 2-methyl-2-{2-methyl-4-[2-(5-methyl-2-phenyloxazol-4-yl)ethoxy]phenoxy}propionic acid ethyl ester (5.00 g, 11.8 mmol) in THF (30 mL) and MeOH (60 mL) was treated with 5N aqueous NaOH (20 mL). The solution was heated at 55° C. for 1 h, cooled to ambient temperature, and concentrated in vacuo. The residue was treated with ice water (20 mL), acidified with 5N aqueous HCl (25 mL), and extracted with ethyl acetate (200 mL). The organic layer was washed with brine (40 mL), dried (Na2SO4), and concentrated to a white solid (4.46 g, 96%): mp 117° C.; 1H NMR (400 MHz, CDCl3) δ 1.53 (s, 6H), 2.19 (s, 3H), 2.38 (s, 3H), 2.98 (t, 2H, J=6.6 Hz), 4.15 (t, 2H, J=6.6 Hz), 6.58 (dd, 1H, J=3.4, 8.8 Hz), 6.70 (d, 1H, J=2.9 Hz), 6.80 (d, 1H, J=8.8 Hz), 7.38-7.45 (m, 3H), 7.97-8.00 (m, 2H); MS (FIA) m/e 394.2 [M−1].

Workup

temperaturecooled to ambient temperature
concentrationconcentrated in vacuo
additionThe residue was treated with ice water (20 mL)
extractionextracted with ethyl acetate (200 mL)
washThe organic layer was washed with brine (40 mL)
dry with materialdried (Na2SO4)
concentrationconcentrated to a white solid (4.46 g, 96%)

Sources & evidence

ORD record: ord-3cae4ddcb5ee426cb7a81de098b630c9
Source dataset: uspto-grants-2006_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06982278B2

Reaction notes

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