Hydrochloric Acid → HCID 86641128, compound

Participants

Reaction Steps

Compound 36.3 (129 mg, 0.22 mmol) was dissolved in 2.2 mL anhydrous DMSO, treated with TFA.Pyridine (11 mg, 0.056 mmol) and DCC (69 mg, 0.33 mmol). The mixture was stirred at r.t. for 14 h, and then cooled to 0° C. Premixed (EtO)2P(O)CH2P(O)(OEt)2 with 1 M t-BuOK in THF (0.345 mL, 0.34 mmol) at 0° C., the mixture was stirred for 5 min and then added to the oxidized reaction mixture, warmed to r.t. and stirred for 3 h. The mixture was then cooled to 0° C., treated with 0.4 mL 1N HCl, diluted with EtOAc. The organic layer was washed with saturated NaHCO3, brine, dried over MgSO4, filtered and concentrated under reduced pressure. The residue was subjected to a silica gel column chromatography eluting with EtOAc to give compound 36.4 (124 mg, 81% yield).

Provenance & Evidence