Pyridine → HCID 131714550, compound

Participants

Reaction Conditions

Reaction Steps

Benzyl-N-(4-benzyloxyphenyl)glycinate (694 mg, 2.0 mmole) was dissolved in 6 ml of dry toluene and cooled to 0° C. A phosgene solution (2.9 ml, 12.5% in toluene) was added to the reaction mixture followed by the dropwise solution of pyridine (0.348 ml, 4.3 mmol) with rapid stirring. The reaction was stirred for 1.5 hours at 0° C. and then allowed to warm to room temperature. The precipitate of pyridinium hydrochloride was filtered under argon, and the volatiles were removed from the filtrate. This was dissolved in 4 ml of dry tetrahydrofuran and cooled to 0° C. To this solution was added (S)-3-[[(phenylmethoxy)carbonyl]amino]-2-azetidinone (440 mg, 2.0 mmole) and 36 mg (0.3 mmole) of dimethylaminopyridine. Triethylamine (0.307 ml, 2.2 mmol) was then added dropwise, and the reaction mixture was allowed to warm to room temperature and stir overnight. The product was extracted with ethyl acetate from dilute aqueous hydrochloric acid. The combined organic extracts were dried with sodium sulfate and the volatiles removed. The residue was purified by flash chromatography on silica (LPS-1) (eluting with 1:1 ethyl acetate/hexane) to yield 465 mg of the title compound.

Provenance & Evidence