Potassium methyl N-cyanodithioimidocarbonate → 3-(4-Amino-2-methylsulfanyl-thiazol-5-yl)-2-cyano-3-oxo-propionic acid tert-butyl ester

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Reaction Steps

To a stirred solution of 4-chloro-2-cyano-3-hydroxy-but-2-enoic acid tert-butyl ester Compound 1c (51.3 g, 236 mmol) at 0° C. in acetone (750 mL) was added potassium methyl N-cyanodithioimidocarbonate Compound 1e (40.2 g, 236 mmol). After 1 hr the reaction was allowed to warm to RT. The reaction mixture was evaporated down after stirring for 18 hrs. The resulting residue was extracted with ethyl acetate from saturated NaHCO3. The combined organic layers were dried over MgSO4 and the solvent removed under reduced pressure to yield a tan foam, 3-(4-amino-2-methylsulfanyl-thiazol-5-yl)-2-cyano-3-oxo-propionic acid tert-butyl ester Compound 1h, 72.2 g. 1H NMR (CDCl3) δ 4.34 (br s, 2H), 3.14 (br s, 1H), 2.70 (br s, 3H), 1.47 (br s, 9H). MS 314 (MH+).

Provenance & Evidence