Piperidine → 4-((R)-2-methyl-1-thioureidopropyl)-N-(tetrahydro-2H-pyran-2-yloxy)benzamide

Participants

Reaction Conditions

Reaction Steps

A solution of 4-((R)-1-amino-2-methylpropyl)-N-(tetrahydro-2H-pyran-2-yloxy)benzamide (0.1643 g, 0.562 mmol) and N,N-diisopropylethylamine (0.1 mL, 0.6 mmol) in DCM (2.5 mL) was cooled in an ice bath and added to a solution of Fmoc-isothiocyanate (0.173 g, 0.616 mmol) in DCM (2.5 mL, 38 mmol) cooled at 0° C. in an ice bath. The reaction solution was stirred at rt for 1 h. Piperidine (1.0 mL, 2.0 mmol, 2.0 M in MeOH) was then added and the reaction stirred at rt for an additional 2 h. The reaction was concentrated and the residue was purified by flash chromatography (EtOAc:hex, 7:3 to 1:0) to afford 4-((R)-2-methyl-1-thioureidopropyl)-N-(tetrahydro-2H-pyran-2-yloxy)benzamide as a white solid. LC-MS: (FA) ES+ 352.

Provenance & Evidence