Triethylamine → Carbamic acid, [1-[(methoxymethylamino)carbonyl]-3-pentynyl]-, 1,1-dimethylethyl ester

Participants

Reaction Steps

The product from Step D (10.58 g, 46.6 mmol), N,O-dimethylhydroxylamine hydrochloride (9.09 g, 93.2 mmol), HOBT hydrate (9.44 g, 69.9 mmol) and triethylamine (13.0 mL, 93.2 mmol) were stirred in dry DMF (150 mL) at 0° C. under nitrogen. EDC hydrochloride (11.5 g, 60.6 mmol) was added, and the reaction was stirred for 3 hours. The solution was partitioned between 2:1 ethyl acetate:hexane and water, washed with water, 10% aq. HCl, sat. NaHCO3 soln and brine, then dried with sodium sulfate. The solvent was removed in vacuo to give the title compound as an orange oil

Provenance & Evidence