Pyridine → HCID 57827501, compound

Participants

Reaction Conditions

Reaction Steps

N-(((3S,4R,5S)-5-(fluoromethyl)-3-(2-fluorophenyl)-4-(hydroxymethyl)tetrahydrofuran-3-yl)carbamothioyl)benzamide (78.70 g, 193.63 mmol) was dissolved in pyridine (391 mL, 5190.48 mmol), and the mixture cooled to 0° C. Trifluoromethanesulfonic anhydride (43.98 mL, 261.40 mmol) was added dropwise over 40 min (internal temperature increased from 4° C. to 18° C.). The reaction was stirred in an ice bath for 1 h and 25 mins. It was quenched by the slow addition of ammonium chloride (sat., aq., 260 mL) and then water (390 mL). The aqueous layer was extracted with EtOAc (3×500 mL). The combined organic extracts were dried over MgSO4, concentrated in vacuo and purified by silica gel column chromatography (20% to 60% EtOAc/hex) to obtain the title compound (70.86 g, 94%). 1H NMR (400 MHz, CDCl3) δ ppm 2.83 (dd, J=13.64, 3.79 Hz, 1H) 3.30 (dd, J=13.89, 3.54 Hz, 1H) 3.38-3.47 (m, 1H) 4.07 (dd, J=9.22, 2.65 Hz, 1H) 4.51-4.78 (m, 4H) 7.15 (ddd, J=12.44, 8.15, 1.14 Hz, 1H) 7.22 (td, J=7.58, 1.26 Hz, 1H) 7.34-7.41 (m, 1H) 7.41-7.48 (m, 3H) 7.49-7.56 (m, 1H) 8.10-8.18 (m, 2H).

Provenance & Evidence