Bromotrimethylsilane → HCID 21972597, compound

Participants

Reaction Steps

A suspension of [2-[(2-amino-3,4-dioxo-1-cyclobuten-1-yl)methylamino]ethyl]phosphonic acid diethyl ester (600 mg, 2.3 mmol) in anhydrous 1,2-dichloroethane (20 mL) under nitrogen was treated with bromotrimethylsilane (2.0 mL, 15 mmol) and heated to reflux for 10 minutes. The yellow solution was concentrated and the resulting solid was dissolved in water (75 mL), washed with diethyl ether (2×50 mL) and evaporated. The solid was dissolved in boiling methanol, filtered, and concentrated with the addition of ethyl acetate to a final volume of 75 mL to afford the title compound as a yellow solid (310 mg, 58%, mp 230°-260° C. dec); IR (KBr, cm-1): 3340, 1800; MS (-FAB): 233 (M-H, 32), 148 (100); 1H NMR (DMSO, 400 MHz): δ 7.62 (br s, NH2), 3.68 (br s, 2H), 3.16 (br s, 3 H), 1.90 (d of t,J=18 and 7.5 Hz, 2H).

Provenance & Evidence