Citric Acid → HCID 22273522, compound

Participants

Reaction Steps

A suspension of {N-[2-(methoxymethoxy)ethyl)]carbamoyloxymethyl}phenyl (Method 38, 2.4 g, 10 mmol) and 10% palladium on carbon (300 mg) in THF (20 ml) was stirred under an atmosphere of hydrogen at ambient temperature for 18 hours. The catalyst was removed by filtration and the filtrate was placed under nitrogen. Triethylamine (1 ml, 7.5 mmol) and 4-iodophenylsulphonyl chloride (1.82 g, 6 mmol) were added and the mixture was stirred at ambient temperature for 2 hours. The reaction mixture was poured into a mixture of EtOAc (30 ml) and 1M aqueous citric acid solution (30 ml). The phases were separated and the aqueous phase washed with EtOAc (30 ml). The organic extracts were combined, washed 1M aqueous citric acid solution (2×30 ml), brine (30 ml), dried and the volatiles removed by evaporation to yield the title compound (2.18 g, 98%) as a waxy solid. NMR 3.15 (q, 2H), 3.31 (s, 3H), 3.59 (t, 2H), 4.53 (s, 2H), 4.96 (t, 1H), 7.58 (d, 2H), 7.90 (d, 2H); m/z 370 (M−H)−.

Provenance & Evidence