Diethyl Ether → Methyl 2-(1-((tert-butoxycarbonyl)amino)ethyl)thiazole-5-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-(1-(tert-butoxycarbonylamino)ethyl)thiazole-5-carboxylic acid (1.03 g, 3.8 mmol) in a mixture of MeOH (20 mL) and toluene (20 mL) cooled to 0° C. was added dropwise 2.0M trimethylsilyldiazomethane in ether (12 mL, 24 mmol). The resulting reaction mixture was warmed to room temperature overnight. Excess trimethylsilyldiazomethane was quenched with the addition of acetic acid and the solution concentrated to dryness. The residue was partitioned between EtOAc and saturated aqueous NaHCO3, the organic layer dried over anhydrous Mg2SO4 and concentrated to afford a yellow oil (0.90 g, 83%). LC-MS: (FA) ES+ 287.

Provenance & Evidence