Sodium Methoxide → 4-Propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide

Participants

Reaction Steps

A solution of freshly prepared sodium methoxide (6.41 g, from 2.3 g of Na) in 100 ml of methanol was added a solution of N-(aminosulfonyl)-DL-valine methyl ester (16.6 g; 0.079 mmol) in methanol (150 ml) and the resulting reaction mixture was stirred for 6 hours. The mixture was cooled, neutralized with BIO-RAD® 50W-X8 H+ ion exchange resin, and filtered. The filtrate was concentrated in vacuo to afford 16.4 g of a crude 4-isopropyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (Formula IV: R1 =H; R2 =isopropyl; R3 =H).

Provenance & Evidence