Ethyl Acetate → HCID 67508114, compound

Participants

Reaction Steps

In a flask, 3-(Benzyloxycarbonylamino)-3-methylbutanoic acid (14.77 g, 58.8 mmol, prepared as described in Low, Eddy; Nair, Satheesh; Shiau, Timothy; Belisle, Barbara; Debabov, Dmitri; Celeri, Chris; Zuck, Meghan; Najafi, Ron; Georgopapadakou, Nafsika; Jain, Rakesh Bioorganic and Medicinal Chemistry Letters, 2009, 19, 196-198) was dissolved in tetrahydrofuran (200 ml). N,N-dicarbonyldiimidazole (9.54 g, 58.8 mmol) was added to the mixture, and the combined reaction mixture was stirred for about 1 hour at room temperature. In a second flask, lithium bis(trimethylsilyl)amide (1.0 M in tetrahydronfuran, 117 ml, 117 mmol) was cooled to −78° C., and ethylacetate was slowly added. The second flask was stirred for 20 minutes and then added to the first flask, which was also cooled to −78° C. The combined mixture was stirred at −78° C., for 2 hours. The reaction mixture was quenched with saturated, aqueous NaHCO3 solution, and the mixture was extracted with ethylacetate. The ethylacetate layer was concentrated, and purified by column chromatography (0 to 20% ethylacetate in hexanes) to give 10.08 g (53%) of the title compound.

Provenance & Evidence