Ammonium Chloride → HCID 178494774, compound

Participants

Reaction Steps

To a suspension of (methoxymethyl) triphenylphosphonium chloride (0.83 g, 2.43 mmol) in anhydride tetrahydrofuran (4.3 mL) was added dropwise a solution of lithium bis(trimethylsilyl) amide 1M (2.43 mL, 2.43 mmol) at 0° C. under nitrogen atmosphere. The mixture was stirred for 30 minutes, then a solution of trans-4-((3-(2-chloro-4-formyl-5-methoxyphenylamino)-3-oxopropyl)(methyl)amino)cyclohexyl hydroxy(di-2-thienyl)acetate (intermediate 43; 0.41 g, 0.69 mmol) in anhydride tetrahydrofuran (2.1 mL) was added dropwise into the mixture. The reaction was stirred for 30 minutes at 0° C. and for 1.5 hours at room temperature. The crude was added into a saturated solution of ammonium chloride and extracted with ethyl acetate. The organic layer was washed with water, brine, dried and the solvent was removed under reduced pressure giving an orange solid. This crude was purified by column chromatography with silica gel, eluting with methylene chloride/isopropanol (93:7) to give the title compound as a white solid (56%).

Provenance & Evidence