Trichloroacetonitrile → [2-Phenyl-1-(thiophene-2-sulfonylamino)-ethyl]-phosphonic acid mono-(2-chloropyridin-3-yl) ester ammonium salt

Participants

Reaction Conditions

Reaction Steps

To a sealed tube containing phosphonic acid (xiii) (134 mg; 0.39 mmol) and 2-chloro-3-pyridinol (60 mg; 0.46 mmol) was added pyridine (1.9 mL) and trichloroacetonitrile (270 μL; 2.7 mmol). The reaction was heated to 105° C. for 6 hours then was cooled and concentrated. The residue was purified by flash chromatography (chloroform-methanol-concentrated ammonium hydroxide; 9:2:0.1) to yield the ammonium salt 46 (100 mg, 54%) as a colorless solid: 1H NMR: (400 MHz, CD3OD) δH 2.87 (td, J=9, 14 Hz, 1H, CHPh), 3.28-3.36 (m, 1H, CHPh), 4.01 (ddd, J=4.5, 9, 17 Hz, 1H, NCHP), 6.81 (dd, J=3.5, 5 Hz, 1H, Ar—H), 7.07-7.21 (m, 6H. Ar—H), 7.28 (dd, J=4.5, 8 Hz, 1H, Ar—H), 7.46 (dd, J=1.5, 5 Hz, 1H, Ar—H), 7.91-7.93 (m, 1H, Ar—H), 7.99-8.02 (m, 1H, Ar—H); 31P NMR: (162 MHz, CD3OD) δP 17.0; 13C NMR: (100 MHz, DMSO-D6) δC 38.3, 55.6, (d J=147.6 Hz), 124.3, 126.7, 128.1, 130.1, 130.4, 131.8, 132.1, 140.3 (d, J=10 Hz), 142.4, 142.7, 144.5, 147.9.

Provenance & Evidence