Pyridine → HCID 72247373, compound

Participants

Reaction Steps

Compound 6.3 (1.2 g, 2.91 mmol) was dissolved in 23 mL DMSO, and treated with DCC (3.6 g, 17.5 mmol) and DCA (0.24 mL, 2.91 mmol). The mixture was stirred for 2 h and then treated with 0.3 mL pyridine. Diethyl(triphenylphosphoranylidene)methylphosphonate (2.9 g, 6.98 mmol) was dissolved in 5 mL CH2Cl2 and it was added to the mixture dropwise and the mixture was stirred for 3 h. The mixture was concentrated under reduced pressure and the residue was dissolved in EtOAc. The organic layer was washed with H2O three times, dried over MgSO4, filtered and concentrated down under reduced pressure. The residue was subjected to a silica gel column chromatography eluting with 100% EtOAc to 5% MeOH in EtOAc to give compound 6.4 (469 mg, 30% yield). 1HNMR (300 MHz, CD3OD) δ 1.17-1.35 (m, 6H), 1.46 (s, 3H), 1.64 (s, 3H), 3.85-3.97 (m, 4H), 4.04-4.12 (m, 1H), 5.01 (m, 1H), 5.33-5.45 (m, 2H), 5.81 (d, 1H, J=5.7), 6.63-6.77 (m. 1H), 7.57-8.12 (m, 5H), 8.87 (s, 1H). LRMS (ESI) MH+ C24H29N6O7P requires 545.2, Found 545.0.

Provenance & Evidence