Glycine → {[7-Hydroxy-4-(3-methoxy-phenyl)-2-phenyl-oxazolo[4,5-c]pyridine-6-carbonyl]-amino}-acetic acid

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Reaction Steps

Sodium methoxide methanol solution (0.5 N, 0.4 mL, 0.2 mmol) was added to a solution of 7-(2,2-dimethyl-propionyloxy)-4-(3-methoxy-phenyl)-2-phenyl-oxazolo[4,5-c]pyridine-6-carboxylic acid methyl ester (7.5 mg, 0.016 mmol), and 7-hydroxy-4-(3-methoxy-phenyl)-2-phenyl-oxazolo[4,5-c]pyridine-6-carboxylic acid methyl ester (24.7 mg, 0.066 mmol) in methanol (2 mL) at room temperature. After the reaction mixture was refluxed for 1 hour, the mixture was concentrated. To the residue glycine (0.129 g, 1.72 mmol) and sodium methoxide methanol solution (0.5 N, 2.88 mL, 1.44 mmol) were then added. The mixture was then refluxed overnight, cooled, and concentrated. The residue was dissolved in water (30 mL), and the solution was washed with ethyl acetate (3×20 mL). After the solution was acidified to pH 1-2 with 2N HCl, a light yellow solid precipitated, that was collected by filtration and then dried in vacuo to give 23.5 mg of the title compound. MS: (−) m/z 417.9 (M−1).

Provenance & Evidence