Lawesson's reagent → HCID 10222841, compound

Participants

Reaction Steps

N-[2-(Benzyloxy)benzoyl]-L-serine benzyl ester (20 mg, 0.05 mmol) and Lawesson's reagent [2,4-bis(p-methoxyphenyl)-1,3-dithiadiphosphetane-2,4-disulfide] (20 mg, 0.05 mmol, 1 equiv.) were dissolved in toluene (15 mL). After being refluxed overnight under nitrogen, the reaction mixture was diluted with EtOAc (20 mL), washed with brine, dried over MgSO4, filtered, concentrated and chromatographed on silica gel eluting with hexanes/EtOAc (6/1) to yield thiazoline (7) as a clear oil. Rf=0.3 (hexanes/EtOAc, 6:1); 1H NMR (300 MHz, CDCl3) δ8.00 (dd, 1H, ArH), 7.51-7.49 (m, 2H, ArH), 7.42-7.25 (m, 9H, ArH), 7.02-6.95 (m, 2H, ArH), 5.28 (d, 1H, PhCHH), 5.20 (d, 1H, PhCHH), 5.18 (s, 2H, CH2Ph), 5.12 (dd, 1H, CHCH2), 3.60-3.47 (m, 2H, CHCH2); MS (FAB) m/z 404 MH+, measured exact mass: 404.1313, calculated exact mass: 404.1320.

Provenance & Evidence