Lawesson's reagent → HCID 60054126, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of methyl 6-[(5S)-5-[(acetylamino)methyl]-2-oxo-3-oxazolidinyl]-3,4-dihydro-2(1H)-isoquinolinecarboxylate (Example 1, 280 mg, 0.806 mmol) and Lawesson's reagent (179 mg, 0.443 mmol) in dry THF (8.1 mL) under N2 is heated up to 60° C. over 15 mins, stirred at this temperature for 5 mins, and then cooled to ambient temperature and concentrated under reduced pressure. The crude product mixture is then chromatographed on a Flash 40S silica gel (40 g, 32-63 μm) cartridge, eluting with MeOH/CH2Cl2 (2/98), and those fractions with an Rf=0.57 by TLC (MeOH/CHCl3, 10/90) are pooled and concentrated and the residue recrystallized from CH2Cl2/Et2O to give 216 mg (74%) of the title compound as an off-white solid, mp 149-150° C. (dec.); [α]25D=5° (c 0.99, DMSO).

Provenance & Evidence