N-(Diphenylmethylene)glycine tert-butyl ester → HCID 68551405, compound

Temperature

0 °C

660 mg of N-(diphenylmethylene)glycine tert-butyl ester (2.23 mmol, 1.0 equiv.) were dissolved in 15 ml of dry THF and cooled to 0° C. under argon. Then 2.23 ml of 1 M lithium hexamethyldisilazane (LiHMDS) solution in THF were added dropwise, and the mixture was stirred at 0° C. for 15 min. Subsequently, 642 mg of tert-butyl (5-bromomethylpyridin-2-yl)-carbamate (2.23 mmol, 1.0 equiv.) were added, and the mixture was stirred at 0° C. for 2 h. The mixture was quenched with 18 ml of sat. citric acid and stirred at RT for 1 h. The mixture was extracted with ethyl acetate (2×30 ml), and the organic phases were washed with 50 ml of 1 M HCl. The aqueous phases were combined and adjusted to pH 10 with 2M NaOH and then extracted 3× with ethyl acetate. The combined organic phases were dried over Na2SO4 and concentrated. The residue was purified by flash chromatography on silica gel with heptane/ethyl acetate mixtures as eluent. 600 mg (80% yield) of the title compound were obtained as a colorless solid.

1. stirringthe mixture was stirred at 0° C. for 2 h
2. customThe mixture was quenched with 18 ml of sat. citric acid
3. stirringstirred at RT for 1 h
4. extractionThe mixture was extracted with ethyl acetate (2×30 ml)
5. washthe organic phases were washed with 50 ml of 1 M HCl
6. extractionextracted 3× with ethyl acetate
7. dry with materialThe combined organic phases were dried over Na2SO4
8. concentrationconcentrated
9. customThe residue was purified by flash chromatography on silica gel with heptane/ethyl acetate

ORD record

ord-4bd91bda9975474889f60e422b69a046

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08389764B2