Triethylamine → tert-Butyl 4-(2-phenylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecane-9-carboxylate

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Reaction Steps

A solution of tert-butyl 1-oxa-4,9-diazaspiro[5.5]undecane-9-carboxylate hydrochloride (WuXi PharmaTech) (0.60 g) in DMF (11 mL) was treated with triethylamine (1.1 mL), followed by 2-phenyl-1,3-thiazole-4-carboxylic acid (0.421 g) and then O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (1.09 g). The resulting mixture was stirred at RT for 7 h. DMF was removed in vacuo. The residue was taken up in EtOAc (50 mL) and washed with saturated sodium bicarbonate solution (2×30 mL), water (30 mL) and brine (30 mL), dried over sodium sulphate, filtered and evaporated in vacuo. The brown oil was purified by silica gel chromatography eluting with 0-10% MeOH in DCM to give the subtitled compound as a brown solid. Yield 0.857 g.

Provenance & Evidence