Tetrabutylammonium Fluoride → (2S,5R)-6-(allyloxy)-2-(hydroxymethyl)-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-ene-4-carboxamide

Participants

Reaction Steps

(2S,5R)-6-(allyloxy)-2-((tert-butyldimethylsilyloxy)methyl)-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-ene-4-carboxamide (Intermediate 108, 450 mg, 1.2 mmol) was dissolved in THF (about 7 mL); the atmosphere in the reaction vessel was evacuated and backfilled with argon, and the solution was stirred in an ice bath for ten minutes. To it was then added tetrabutylammonium fluoride (1 M in THF) (1.5 mL, 1.5 mmol) dropwise. After one hour, analysis of the mixture by LCMS indicated consumption of starting material and formation of one major product. The mixture was concentrated and dissolved in methylene chloride. Normal-phase chromatography (0-10% methanol in methylene chloride, 25-g column, 25 minutes) was used to isolate the desired product (284 mg, 92%, white solid).

Provenance & Evidence