Hydrochloric Acid → (S)-(-)-N-[[3-[4-[1-(Hydroxyacetyl)-3,6-dihydro-2H-pyridin-4-yl]-3-fluorophenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide

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Reaction Steps

A mixture of (S)-(−)-N-[[2-oxo-3-[3-fluoro-4-[1-[(acetoxy)acetyl]-3,6-dihydro-2H-pyridin-4-yl]phenyl]-5-oxazolidinyl]methyl]acetamide (EXAMPLE 39, 475 mg) and anhydrous potassium carbonate (303 mg) in methanol (44 mL) is stirred under N2 at ambient temperature for 1.5 hours and then adjusted to pH 7 with aqueous hydrochloric acid (1M) and concentrated under reduced pressure. The residue is chromatographed on silica gel (230-400 mesh, 40 g), eluting with a gradient of methanol/chloroform (5/95-10/90), and those fractions with an Rf=0.21 by TLC (methanol/chloroform, 10/90) are pooled and concentrated under reduced pressure. The resulting foam is then triturated with methylene chloride/diethyl either and the precipitate filtered to give the title compound, Anal. calcd for C19H22N8O5F: C, 58.31;H, 5.67; N, 10.74. Found: C, 58.15; H, 5.64; N, 10.72.

Provenance & Evidence