Sodium Hydroxide → 2-Methyl-2-[3-(5-methyl-2-phenyl-oxazol-4-ylmethoxy)-phenyl]-propionic acid

HRID 1994077

Reaction equation

C[O:2][C:3](=[O:27])[C:4]([CH3:26])([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O: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:7]=1)[CH3:5].[OH-].[Na+]>CO.O>[CH3:26][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O: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:7]=1)([CH3:5])[C:3]([OH:27])=[O:2]

Participants

Conditions

Temperature: 70 °C

Procedure

To a stirred solution of the title B compound, 2-methyl-2-[3-(5-methyl-2-phenyl-oxazol-4-ylmethoxy)-phenyl]-propionic acid methyl ester (3.45 g, 9.45 mmol) in methanol (30 mL) is added sodium hydroxide (1.51 g, 37.81 mmol) in water (10 mL) at RT. The reaction mixture is stirred at 70° C. for 4 h. The reaction mixture is concentrated, poured into water, the aqueous layer is separated, washed with ethyl acetate twice, acidified with concentrated HCl and extracted three times with ethyl acetate. The combined ethyl acetate extract is dried over magnesium sulfate and concentrated to give 2-methyl-2-[3-(5-methyl-2-phenyl-oxazol-4-ylmethoxy)-phenyl]-propionic acid as a white solid.

Workup

concentrationThe reaction mixture is concentrated
additionpoured into water
customthe aqueous layer is separated
washwashed with ethyl acetate twice
extractionextracted three times with ethyl acetate
extractionThe combined ethyl acetate extract
dry with materialis dried over magnesium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-06c929a5838d4b8285a53cb4ea39bf8c
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07652061B2

Linked notes

Loading…