Ethyl Acetate → HCID 67508114, compound

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.

1. customthe combined reaction mixture
2. stirringThe second flask was stirred for 20 minutes
3. additionadded to the first flask, which
4. temperaturewas also cooled to −78° C
5. stirringThe combined mixture was stirred at −78° C., for 2 hours
6. customThe reaction mixture was quenched with saturated, aqueous NaHCO3 solution
7. extractionthe mixture was extracted with ethylacetate
8. concentrationThe ethylacetate layer was concentrated
9. custompurified by column chromatography (0 to 20% ethylacetate in hexanes)

ORD record

ord-736c8745c3af45ec9dda4ae9ac41a98d

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09248117B2