Triphenylphosphine → HCID 15542665, compound

Participants

Reaction Steps

A solution of allyl (1S,5R,6S)-6-[1(R)-allyloxycarbonyloxy-ethyl]-2-hydroxymethyl-1-methyl-carbapen-2-em-3-carboxylate (64.8 mg, 0.174 mmol), 1,1-dioxo-2,3-dihydro-naphtho[1,8de][1,2]thiazin-3-one (34.5 mg, 0.145 mmol), and triphenylphosphine (46 mg, 0.174 mmol) in anhydrous tetrahydrofuran (2 mL) was cooled in an ice bath and stirred under a nitrogen atmosphere. Diisopropyl azodicarboxylate (0.034 mL, 0.174 mmol) was added and the resulting mixture was stirred at 0-5° C for 10 minutes. The mixture was concentrated under vacuum and the residue was purified by preparative layer chromatography on a 1 mm×20 cm×20 cm silica gel GF plate using 7:3 ethyl acetate-hexanes as the developing solvent. The product band was removed and eluted with ethyl acetate to afford allyl (1S,5R,6S)-6-[1(R)-allyloxycarbonyloxy-ethyl]-1-methyl-2-(1,1,3-trioxo-2,3-dihydro-naphtho[1,8-de][1,2]thiazin-2-ylmethyl)-carbapen-2-em-3-carboxylate (49 mg) as an oil.

Provenance & Evidence