Glycine → [(7-Hydroxy-4-methyl-2-phenyl-thiazolo[5,4-c]pyridine-6-carbonyl)-amino]-acetic acid

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A mixture of 7-hydroxy-4-methyl-2-phenyl-thiazolo[5,4-c]pyridine-6-carboxylic acid ethyl ester (105 mg, 0.33 mmole) and glycine (500 mg, 6.65 mmole) in 0.5 M sodium methoxide/methanol (12.6 ml) was refluxed for 3 days before it was cooled to room temperature and concentrated in vacuo. The residue was dissolved in water (30 ml) and extracted twice with methyl t-butyl ether. The remaining aqueous layer was acidified to pH=3 with 1N HCl (9 ml). The resulting precipitate was filtered, washed with water and dried in vacuo to give the title compound as a yellow solid (25 mg): 1H NMR (DMSO-d6, 200 MHz): δ=13.08 (br s, 1H), 9.22 (t, 1H), 8.13 (m, 2H), 7.61 (m, 3H), 4.02 (d, J=6.2 Hz, 2H), 2.72 (s, 3H); MS: (+) m/z 344.26 (M+1).

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