Hydrochloric Acid → HCID 59778412, compound

Participants

Reaction Steps

To a solution of (S)-2-(methyl(tert-butoxycarbonyl)amino)propyl 4-ethylphenylcarbamate (105 mg, 0.27 mmol) in MeOH was added HCl (4M in dioxane, 0.2 mL, 0.81 mmol, 3 equiv.) and the mixture was stirred for 2 h. LC/MS indicated the reaction was complete and the mixture was concentrated under reduced pressure to give a crude oil, which was re-dissolved in THF. To this THF solution was added 4-ethylphenyl isocyanate (30 μL, 0.26 mmol) followed by DIEA (0.11 mL, 0.66 mmol, 2.5 equiv.). The reaction mixture was stirred for 2 h. LC/MS indicated the completion of the reaction. The mixture was filtered and the filtrate was purified on RP-HPLC using a mixture of acetonitrile and H2O to give (S)-2-(3-(2-chlorobenzyl)-1-methylureido)propyl 4-ethylphenylcarbamate (88.6 mg, 81% for two steps). LRMS (M+H+) m/z 404.1.

Provenance & Evidence