Water → HCID 54424107, compound

Participants

Reaction Steps

A solution of (R)-(-)-4-[4-[5-(azidomethyl)-2-oxo-3-oxazolidinyl]-2-fluorophenyl]-1-piperidinecarboxylic acid 1,1-dimethylethyl ester (EXAMPLE 20, Step 7, 12.05 g) in dry tetrahydrofuran (96 mL) under N2 is treated with triphenylphosphine (8.29 g) over five minutes, and the resulting mixture is stirred at ambient temperature for two hours. The mixture is then treated with water (3.1 mL), heated up to 40° C., stirred at 40° C. for five hours and at ambient temperature for 12 hours, and then concentrated under reduced pressure to give a viscous oil which is chromatographed on silica gel (70-230 mesh, 500 g), eluting with a gradient of methanol/methylene chloride (2.5/97.5-15/85). Pooling and concentration of those fractions with an Rf =0.26 by TLC (methanol/chloroform, 10/90) gives the title compound, mp 136-137° C.

Provenance & Evidence