Pyridine → HCID 69834954, compound

Participants

Reaction Conditions

Reaction Steps

1-((2R)-2-((tert-Butoxycarbonyl)methylamino)-3-phenylpropionyl)-2-ethoxycarbonylformylhydrazine (1.4 g, 3.55 mmol) was dissolved in ether (25 ml) and THF (10 ml). Pyridine (1.44 ml 17.75 mmol) was added, and the solution was cooled to 0° C. Thionyl chloride (0.3 ml, 3.90 mmol) was added dropwise. The reaction mixture was stirred at 0° C. for 2 h. The precipitation was filtered off. The solvent was removed in vacuo without warming. The residue was dissolved in toluene (25 ml) and the solution was warmed to reflux for 2 h. The solvent was removed in vacuo. The crude product was purified by flash chromatography on silica (70 g) with ethyl acetate/dichloromethane 1:2 to give 721 mg of 5-((1R)-1-((tert-butoxycarbonyl)methylamino)-2-phenylethyl)-[1,3,4]oxadiazole-2-carboxylic acid ethylester.

Provenance & Evidence