2-Propanol, 2-methyl-, lithium salt (1:1) → (S)-N-((3-(3-fluoro-4-(3-(pyridin-2-yl)-1H-pyrazol-1-yl)phenyl)-2-oxooxazolidin-5-yl)methyl)acetamide

Participants

Reaction Steps

The above-described product 20a (1.235 g, 3.18 mmol) and lithium tert-butoxide (0.762 g) were mixed in a reaction vessel. After the air in the vessel was purged with nitrogen, tetrahydrofuran (5 mL) was added into the vessel and the mixture was cooled in an ice-water bath for 5 minutes. Then, methanol (0.204 g, 0.258 mL) was added. Two minutes later, a solution of Compound (11) (1.237 g) in tetrahydrofuran (5 mL) was added. Then, the water-ice bath was removed and the resultant mixture was reacted for 14 hours at room temperature. After completion of the reaction, ethyl acetate was added to the reactant mixture, resulting in a substantial amount of precipitate. Thus obtained mixture was suction-filtered, and the filter cake was recrystallized with a solvent mixture of ethyl acetate/petroleum ether to afford the product 12a (575 mg) as a white powder, with a yield of 45.7%.

Provenance & Evidence