HCID 68595080, compound → HCID 68595970, compound

A solution of Example 128A (1.99 g, 9.34 mmol) in THF (100 mL) was cooled to 0° C. and n-BuLi (3.74 mL of a 2.5M solution in hexanes, 9.34 mmol) was added while maintaining the internal temperature <0° C. The reaction was warmed to ambient temperature and n-BuLi was added twice more (2 mL for each addition). After 30 minutes, the reaction was quenched by addition of water (25 mL) and extracted with MTBE (50 mL). The organic portion was washed with brine (25 mL), dried (Na2SO4), filtered, and concentrated. The residue was purified by silica gel chromatorgraphy (gradient elution: 0-10% MeOH/EtOAc) to give the title compound (490 mg, 2.30 mmol, 25% yield). MS (LCMS) m/z 197 (M-NH2)+.

1. temperaturewhile maintaining the internal temperature <0° C
2. additionfor each addition)
3. customthe reaction was quenched by addition of water (25 mL)
4. extractionextracted with MTBE (50 mL)
5. washThe organic portion was washed with brine (25 mL)
6. dry with materialdried (Na2SO4)
7. filtrationfiltered
8. concentrationconcentrated
9. customThe residue was purified by silica gel chromatorgraphy (gradient elution: 0-10% MeOH/EtOAc)

ORD record

ord-96ebcb41fde342dfb8ba9a20ca17a01d

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08604053B2