Lawesson's reagent → HCID 86670905, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (S)-5-[5-(benzhydrylidene-amino)-2-fluoro-phenyl]-5,7,7-trimethyl-[1,4]oxazepan-3-one (intermediate A17A) (1.15 g, 2.7 mmol) in dioxane (80 ml) at 23° C. was added 2,4-bis-(4-methoxy-phenyl)-[1,3,2,4]dithiadiphosphetane 2,4-disulfide (Lawesson's reagent) (681 mg, 1.7 mmol) and the mixture was stirred at 80° C. for 2 h to obtain a crude solution of the (S)-5-[5-(benzhydrylidene-amino)-2-fluoro-phenyl]-5,7,7-trimethyl-[1,4]oxazepane-3-thione (intermediate A18A), which was cooled to 23° C. and 1 M HCl (3.4 ml, 3.4 mmol) was added. After 30 min of stirring, the reaction mixture was poured on sat. NaHCO3-solution and extracted twice with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered and evaporated to give a dark green oil, which was purified by silica gel column chromatography with dichloromethane/ethyl acetate to give the (S)-5-(5-amino-2-fluoro-phenyl)-5,7,7-trimethyl-[1,4]oxazepane-3-thione (575 mg, 76%) as a light brown foam. MS (ISP): m/z=283.1 [(M+H)+].

Provenance & Evidence