Sodium Hydroxide → 2-{2-Methoxymethyl-4-[2-(5-methyl-2-phenyloxazol-4-yl)ethoxy]phenoxy}-2-methylpropionic acid

HRID 1181139Notes

Reaction equation

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

Participants

Conditions

Temperature: 55 °C

Procedure

A 25 mL round bottomed flask was charged with 2-{2-methoxymethyl-4-[2-(5-methyl-2-phenyloxazol-4-yl)ethoxy]phenoxy}-2-methylpropionic acid ethyl ester (0.039 g, 0.087 mmol), ethanol (2 mL), and then aqueous 2N NaOH (0.22 mL, 0.44 mmol). The solution was heated at 55° C. for 1 h. The mixture was concentrated, acidified using 5% H2SO4 (1.5 mL), and partitioned between CH2Cl2 (15 mL) and brine (15 mL). The organic layer was dried (Na2SO4), filtered, and concentrated and to give a white solid (0.024 g, 66%). MS (ES) m/e 426 (M+1).

Workup

concentrationThe mixture was concentrated
custompartitioned between CH2Cl2 (15 mL) and brine (15 mL)
dry with materialThe organic layer was dried (Na2SO4)
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-7b62bf8cf3234435a636d27ff007fac1
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07282501B2

Reaction notes

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