Hydrochloric Acid → 6-(N-((S)-5-((S)-4-benzyl-2-oxooxazolidin-3-yl)-4-methyl-5-oxopentyl)methylsulfonamido)-5-iodo-N-methyl-2-p-tolylfuro[2,3-b]pyridine-3-carboxamide

Participants

Reaction Conditions

Reaction Steps

To 5-iodo-N-methyl-6-(methylsulfonamido)-2-p-tolylfuro[2,3-b]pyridine-3-carboxamide (1 g, 2.061 mmol) was added (S)-4-benzyl-3-((S)-5-bromo-2-methylpentanoyl)oxazolidin-2-one (0.730 g, 2.061 mmol) and CESIUM CARBONATE (2.014 g, 6.18 mmol) and NaI (0.309 g, 2.061 mmol) and DMA (4.12 mL). Heated 100° C. 2 hr (note: done at 1 hr) Added 30 mL 1N HCl and extracted with EtOAc, washed with brine, and conc. on vac. 3.05 g crude brown oil. Taken up in minimum EtOAc 30 mL and triturated into a stirring solution of 200 mL heptanes. to give a white solid which is filtered. Purified on 120 g Silica: 0-20% DCM/ether 15 column volumes 964 mg 6-(N—((S)-5-((S)-4-benzyl-2-oxooxazolidin-3-yl)-4-methyl-5-oxopentyl)methylsulfonamido)-5-iodo-N-methyl-2-p-tolylfuro[2,3-b]pyridine-3-carboxamide

Provenance & Evidence