Triethylamine → HCID 44819172, compound

Temperature

30 °C

To a solution of Example 18 (step 4) (0.8 g, 2.63 mmol) in dichloromethane (7.6 mL) was added triethylamine (0.78 mL, 5.60 mmol) and methyl 4-bromobutyrate (0.35 mL, 3.04 mmol). The resulting solution was stirred at 30° C. overnight. The reaction mixture was poured into water/dichloromethane (50 mL/50 mL). The crude residue was extracted into dichloromethane. The organic portion was washed with water (50 mL), washed with brine (50 mL), dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The crude product was purified by silica gel flash chromatography using hexane/EtOAc (gradient system) to give the title compound (0.60 g, 57%).

1. extractionThe crude residue was extracted into dichloromethane
2. washThe organic portion was washed with water (50 mL)
3. washwashed with brine (50 mL)
4. dry with materialdried over anhydrous Na2SO4
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customThe crude product was purified by silica gel flash chromatography

ORD record

ord-5a176c43cd944fc8afffb2b591090fd9

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08598359B2