Hydrochloric Acid → 4-[(1-Hydroxy-naphthalene-2-carbonyl)-amino]-tetrahydro-thiopyran-4-carboxylic acid methyl ester

Beteiligte Stoffe

Reaktionsschritte

To a solution of 0.50 g 1-hydroxy-2-naphthoic acid in 5 ml abs. DMF under inert atmosphere 0.18 g 1-hydroxybenzotriazole, 0.71 g 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride and 0.7 ml N,N-diisopropylethylamine were added. After 15 minutes 0.62 g 4-amino-tetrahydro-thiopyran-4-carboxylic acid methyl ester hydrochloride, followed by 0.55 ml N,N-diisopropylethylamine were added. After 16 h at room temperature and 5 h at 60° C. the reaction was poured unto water, adjusted to pH2 with 2 M HCl and extracted with ethyl acetate twice. The combined organic layers were washed with 2M HCl, 2M aqueous sodium carbonate solution and brine. The organic layer was dried over magnesium sulphate, and concentrated to yield 0.92 g of 4-[(1-hydroxy-naphthalene-2-carbonyl)-amino]-tetrahydro-thiopyran-4-carboxylic acid methyl ester.

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