Sodium Hydroxide → HCID 22261153, compound

HRID 1609952Notes

Reaction equation

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

Participants

Conditions

Temperature: 55 °C

Procedure

A solution of 2-methyl-2-{4-[2-(5-methyl-2-phenyloxazol-4-yl)ethoxy]-2-propylphenoxy}propionic acid ethyl ester (0.21 g, 0.5 mmol) in MeOH (10 mL) was treated with 2.5N aqueous NaOH (1.2 mL). The solution was heated at 55° C. for 1.5 h, cooled to ambient temperature, and concentrated in vacuo. The residue was diluted with EtOAc (30 mL) and water (30 mL) and acidified to pH=1 with 5N aqueous HCl. The organic layer was washed with brine (40 mL), dried (Na2SO4), and concentrated to a white solid (0.17 g, 86%). 1H. NMR (400 MHz, CDCl3) δ 7.97 (dd, J=7.4, 2.4 Hz, 2H), 7.44-7.41 (m, 3H), 6.72 (d, J=2.9 Hz, 1H), 6.68-6.59 (m, 2H), 4.59 (s, 2H), 4.14 (t, J=6.6 Hz, 2H), 2.97 (t, J=6.6 Hz, 2H), 2.59 (t, J=7.6 Hz, 2H), 2.38 (s, 3H), 1.61 (q, J=7.7 Hz, 2H), 0.94 (t, J=7.6 Hz, 3H); MS (ES) m/e 396 (M+1).

Workup

temperaturecooled to ambient temperature
concentrationconcentrated in vacuo
additionThe residue was diluted with EtOAc (30 mL) and water (30 mL)
washThe organic layer was washed with brine (40 mL)
dry with materialdried (Na2SO4)
concentrationconcentrated to a white solid (0.17 g, 86%)

Sources & evidence

ORD record: ord-27e50407d88d4c029e2564864def7c9c
Source dataset: uspto-grants-2006_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06982278B2

Reaction notes

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