Ammonium Chloride → Carbamic acid, N-(5-iodo-4-methyl-2-thiazolyl)-, 1,1-dimethylethyl ester

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Reaction Steps

The above prepared 5-iodo-4-methyl-thiazol-2-ylamine (2.768 g, 12 mmol) was dissolved in 30 mL of tBuOH and treated successively with BOC2O (3.02 g, 1.2 eq.), DMAP (0.141 g, 0.1 eq.), and NaHCO3 (3.39 g, 3.5 eq.). After stirring for 18 h at ambient temperature, the reaction mixture was poured onto icewater/NH4Cl, twofold extracted with ethyl acetate, washed with water and brine, dried over magnesium sulfate, and evaporated to dryness. Ensuing flash chromatography (SiO2, hexane/ethyl acetate=8/2), yielded finally 2.383 g of the title compound as off-white foam.

Provenance & Evidence