Ammonia → HCID 22013856, compound

Reaction equation

[OH:1][CH:2]([CH2:7][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][CH:9]=1)[C:3](OC)=[O:4].[NH3:29].[OH-].[Na+]>CO.O1CCCC1>[OH:1][CH:2]([CH2:7][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][CH:9]=1)[C:3]([NH2:29])=[O:4]

Participants

Procedure

Methyl 2-hydroxy-3-[4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]phenyl]propionate (754 mg, 1.98 mmol) obtained in Example 35 was dissolved in methanol-tetrahydrofuran (1:1, 6 ml). 28% Aqueous ammonia (3 ml) was added and the mixture was stirred at room temperature for 2 days. Thereto was added 1N aqueous sodium hydroxide solution (1 ml) and the mixture was stirred for 1 hr. The reaction mixture was partitioned between tetrahydrofuran-ethyl acetate (1:1, 30 ml) and water (10 ml). The organic layer was washed with saturated brine (10 ml), dried over magnesium sulfate and concentrated under reduced pressure to give the title compound (700 mg, yield 96%) as a white solid.