Lithium hydroxide, monohydrate → 605667-95-6

Participants

Reaction Steps

Lithium hydroxide monohydrate (165 mg, 3.9 mmol) was added to a solution of tert-butyl (1-(4-(ethyloxycarbonyl)thiazol-2-yl)ethyl)carbamate (1.4 g crude material) in THF (25 ml) and water (20 ml) and stirred at room temperature for 18 h. A further amount of lithium hydroxide monohydrate was added (165 mg) and stirring continued for 4 h. The THF was removed in vacuo, the aqueous residue acidified with 1N hydrochloric acid and extracted twice with chloroform. The combined organic layers were washed with brine, dried and reduced. Chromatography (50:2:1 chloroform, methanol, acetic acid) and recrystallisation (EtOAc/hexanes) afforded tert-butyl(1-(4-carboxythiazol-2-yl)ethyl)carbamate (686 mg, 64% over two steps).

Provenance & Evidence