Hydrochloric Acid → HCID 12160907, compound

Participants

Reaction Steps

A reaction mixture comprising of tert-butyl prop-2-yn-1-ylcarbamate (219 mg, 1.411 mmol), (azidomethyl)benzene (188 mg, 1.411 mmol), copper (II) acetate (25.6 mg, 0.141 mmol) and sodium L-ascorbate (55.9 mg, 0.282 mmol) in tert-butanol (20 ml)/water (20 ml) was stirred for 18 hours at room temperature. The reaction mixture was acidified to pH1 using 6M HCl, then saturated with solid NaCl. The reaction mixture was concentrated under pressure to yield a green aqueous solution. The mixture was diluted with ethyl acetate and the organics were removed and dried (MgSO4). Concentration under reduced pressure afforded an orange oil. The oil was loaded on to a 10 g SCX2 cartridge, and this was washed with water and methanol. The product was then eluted with 2M ammonia in methanol. The solution was then concentrated to afford the title compound.

Provenance & Evidence