Tetrabutylammonium Fluoride → HCID 57081651, compound

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Reaction Steps

A solution of N-([(5S)-N-(4-[1-(2-trimethylsilylethoxymethyl)pyrrol-2-ylcarbonyl]phenyl)-2-oxooxazolidin-5-yl]methyl)acetamide (0.79 g, 1.72 mM) in dry THF (15 ml) was stirred under nitrogen and treated dropwise with a solution of tetrabutylammonium fluoride in THF (1 M, 8.6 mM). The solution was stirred for 2.5 hours and then heated at reflux for 4 hours. The solution was evaporated and the residue partitioned between EtOAc and water. The organic layer was washed with water, dried (Mg SO4) and evaporated. The residue was purified by column chromatography, eluting with a gradient increasing in polarity from 2% to 10% MeOH/dichloromethane to give the title product as a solid (0.16 g). Mp 202-205° C., MS: 328 (MH+). NMR: 1.97 (3H, s); 3.42 (nH+H2O); 3.58 (2H, t); 3.94 (1H, m); 4.32 (1H, t); 4.89 (1H, m); 6.40 (1H, m); 6.93 (1H, m); 7.32 (1H, m); 7.82 (2H, d); 8.01 (2H, d); 8.37 (1H, t); 12.10 (1H, s).

Provenance & Evidence