Potassium Carbonate → HCID 66716147, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 8.7 g of N-(2-hydroxy-ethyl)-2-nitro-benzenesulfonamide (Skerlj, R. T.; Nan, S.; Zhou, Y.; Bridger, G. J. Tetrahedron Lett. 2002 (43) 7569-7571) in 87 ml of DMF, under argon, was added 8.8 ml of tert-butyl 3-bromopropionate and 14.6 g of K2CO3. The mixture was stirred for 15 hours at 40° C. and a further 5 ml of tert-butyl 3-bromopropionate were then added. The mixture was heated at 40° C. overnight and then filtered through a sinter of porosity 4. The cake was washed with ethyl acetate and the filtrate was then concentrated under reduced pressure and purified by flash chromatography on silica (Merck EasyVarioPrep 400 g column, Si60 15-40 μm), using a gradient of 0 to 10% EtOAc in DCM. The fractions containing the desired product were combined and concentrated under reduced pressure. 9.54 g of tert-butyl 3-[(2-hydroxy-ethyl)-(2-nitro-benzenesulfonyl)-amino]-propionate were obtained. LC/MS (C): tr=3.39 min; [M+Na]+: m/z 397.

Provenance & Evidence