Sulfuric Acid → HCID 68996119, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (S)-hexahydro-[1,2,3]oxathiazolo[3,4-a]pyridine 1,1-dioxide (83 mg, 0.47 mmol), 4-(4-chloro-phenoxy)-phenol (80 mg, 0.36 mmol), and potassium carbonate (99 mg, 0.72 mmol) in DMF (2.5 mL) was heated for 18 h at 65° C. The ambient mixture's pH was adjusted to 1 with an aqueous 20% H2SO4 solution and stirred at ambient temperature for about 20 h. The reaction solution's pH was adjusted to 12-14 with 5N NaOH, and extracted with EtOAc (2×18 mL). The organic layers were combined, dried over anhydrous Na2SO4, and concentrated to an oil. The oil was treated with 2M HCl in ether to give the desired product as a white solid (22 mg, 13%): MS; m/z 318 (MH)+; LCMS (UV) 99% HPLC 99.5%; 1H NMR (400 MHz, DMSO-d6) δ 1.50-1.88 (m, 6H), 2.90-2.97 (m, 1H), 3.25 (d, 1H, J=12.8 Hz), 3.42-3.47 (m, 1H), 4.09-4.13 (dd, 1H J1=7.2 Hz, J2=10.4 Hz), 4.17-4.21 (dd, 1H J1=4 Hz, J2=10.8 Hz)), 6.93-6.96 (m, 2H), 7.06-7.08 (m, 4H); 7.39-7.41 (m, 2H,) 9.155 (s, 2H)

Provenance & Evidence