Sodium Carbonate → 3-[(Furan-2-carbonyl)-amino]-3-{3-[4-(2-methyl-quinolin-4-ylmethoxy)-phenyl]-4,5-dihydro-isoxazol-5-yl}-propionic acid methyl ester

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Reaction Steps

Furan-2-carbonyl chloride ((0.07 g, 0.54 mmol) was added to a mixture of 3-amino-3-{3-[4-(2-methyl-quinolin-4-ylmethoxy)-phenyl]-4,5-dihydro-isoxazol-5-yl}-propionic acid methyl ester di-hydrochloride salt (0.22 g, 0.45 mmol) from step 10e, methylene chloride (10 mL) and aqueous sodium carbonate (5 mL) under a nitrogen atmosphere at room temperature. The reaction was stirred vigorously for 2 h, and partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over magnesium sulfate, and concentrated to give 3-[(furan-2-carbonyl)-amino]-3-{3-[4-(2-methyl-quinolin-4-ylmethoxy)-phenyl]-4,5-dihydro-isoxazol-5-yl}-propionic acid methyl ester (0.23 g, 100%) as an oil. MS found: (M+H)+=514.

Provenance & Evidence