Bicarbonate Ion → Tert-butyl(3-(3-methylthioureido)propyl)carbamate

Participants

Reaction Steps

To a solution of tert-butyl(3-thioureidopropyl)carbamate (0.29 g, 1.28 mmol) in MeOH (8 mL) was added iodomethane (80 μL, 1.29 mmol). After stirring at rt for 18 h, bicarbonate on polymer support (0.5 g, 3.5 mmol NaCO3/g resin) was added to the reaction mixture. After 30 min, the reaction mixture was filtered, and the filtrate was concentrated in vacuo to give the desired product along with the N-methylated product, tert-butyl (3-(3-methylthioureido)propyl)carbamate (0.28 g, 87%, 2:1 ratio). The crude residue was used as such in the following step. LCMS: Rt=0.44 min and 0.49 min, m/z=248.1 (M+1) Method 2m_acidic.

Provenance & Evidence