(2-Amino-4,5-dimethylthiophen-3-yl)(4-chlorophenyl)methanone → tert-Butyl 3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-((3-(4-chlorobenzoyl)-4,5-dimethylthiophen-2-yl)carbamoyl)-azetidine-1-carboxylate

Participants

Reaction Steps

To a solution of 3-(((9H-fluoren-9-yl)methoxy)carbonylamino)-1-(tert-butoxycarbonyl)azetidine-3-carboxylic acid (0.438 g, 0.999 mmol), and (2-amino-4,5-dimethylthiophen-3-yl)(4-chlorophenyl)methanone (0.241 g, 0.908 mmol) in DCM (20 mL) at 0° C. was added N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (EDC.HCl) (209 mg, 1.090 mmol). The reaction was warmed to rt and stirred overnight, before it was concentrated to dryness. The residue was purified by flash chromatography (hexane/EtOAc) to give tert-Butyl 3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-((3-(4-chlorobenzoyl)-4,5-dimethylthiophen-2-yl)carbamoyl)-azetidine-1-carboxylate as an orange oil (382 mg). LRMS (M+Na)+: 708 m/z.

Provenance & Evidence