Triethylamine → HCID 11690038, compound

Participants

Reaction Steps

To a solution of the product from step (ii) (0.688 g) in MeCN (5 ml) was added triethylamine (1.39 ml) and methanesulfonyl chloride (0.54 ml) and the reaction stirred at rt for 5 h. Further triethylamine (0.83 ml) and methanesulfonyl chloride (0.54 ml) were added and the reaction stirred for 16 h. The residue was partitioned between ethylacetate/water, the organics were separated, washed with 2M hydrochloric acid, sodium hydrogencarbonate solution, brine, dried and evaporated under reduced pressure. The residue was purified by chromatography on silica eluting with 30-40% ethylacetate/iso-hexane to give a mixture of mono- and di-methanesulfonamides. This was dissolved in THF (2 ml) and a solution of 1 M sodium hydroxide (4 ml) was added and the reaction heated at 55° C. for 2 h. After cooling to RT, water (10 ml) was added and the solution extracted with ethylacetate. The aqueous solution was acidified with 2M hydrochloric acid and extracted with ethylacetate. These later organics were dried and evaporated under reduced pressure. Yield 302 mg

Provenance & Evidence