Potassium Carbonate → HCID 178438920, compound

Participants

Reaction Steps

(S)-Arginine (12.6 g) and K2CO3 (12.03 g) are suspended in 50% water/dioxan (250 ml) with vigorous stirring and the reaction mixture is cooled to <5° C. 3-(α,α-Dimethylbenzyl)benzenesulphonyl chloride (21.4g) is added in 6 portions over 30 minutes at <5° C. The mixture is stirred at 20° C. for 2 hours. A colourless solid precipitates. The dioxan is removed by evaporation and the aqueous residue is acidified with cone. HCl. The mixture is extracted with ethyl acetate (3×50ml) and the aqueous phase and all solid materials are combined and neutralised (4M NaOH). The suspension is stirred for 16 hours at 20° C. The solid precipitate is collected by filtration and stirred for 16 hours with a little water. The solid is collected by filtration and dried (NaOH pellets) to give Nα -(3-(α,α-dimethylbenzyl)benzenesulphonyl)-(S)-arginine, m.p. 122°-124° C. (Found: C, 53.49; H, 6.81; N, 11.92; S, 6.93. C21H28N4O4S.2.3H2O requires C, 53.22; H, 6.93; N, 11.82; S, 6.77%).

Provenance & Evidence