Benzoyl isothiocyanate → HCID 89573589, compound

Participants

Reaction Steps

A solution of ((3S,4S)-4-amino-7-fluoro-4-methylchroman-3-yl)methanol from step F3 (795 mg, 3.76 mmol), and benzoyl isothiocyanate (614 mg, 3.76 mmol) in THF (50 mL) was stirred at rt for 1.5 h. The resulting mixture was concentrated in vacuo. The crude residue was purified using silica gel column chromatography (95:5 chloroform/MeOH) to afford rel-N-(((3S,4S)-7-fluoro-3-(hydroxymethyl)-4-methylchroman-4-yl)carbamothioyl)benzamide (1.32 g, 3.53 mmol, 94% yield). LCMS (M+Na)+=397.2. 1H NMR (500 MHz, DMSO-d6) δ 11.45 (s, 1H), 11.26 (s, 1H), 7.91 (dd, J=8.4, 1.2 Hz, 2H), 7.68-7.58 (m, 1H), 7.57-7.41 (m, 3H), 6.86 (td, J=8.5, 2.7 Hz, 1H), 6.70 (dd, J=10.4, 2.7 Hz, 1H), 4.84 (t, J=4.7 Hz, 1H), 4.56 (dd, J=11.4, 3.1 Hz, 1H), 4.20 (dd, J=11.4, 1.6 Hz, 1H), 3.64-3.52 (m, 1H), 3.26-3.12 (m, 2H), 2.07 (s, 2H).

Provenance & Evidence