Tetrahydrofuran → HCID 86699929, compound

Temperature

-78 °C

Under argon atmosphere, at −78° C., to a stirred solution of methyl-2-[tert-butoxycarbonyl-(propanoyl)-amino]-acetate (0.856 g, 3.5 mmol) in dry THF (4 mL) was initially added DMPU (0.89 g, 7.0 mmol) followed by LHMDS (1M solution in THF, 8.75 mL, 8.75 mmol) over a period of 10 min. After stirring at −78° C. for 1.5 h, the reaction mixture was quenched with saturated NH4Cl solution and extracted with AcOEt (3×15 mL). The organic layer was washed with H2O and brine, dried over Na2SO4, filtered, and concentrated in vacuo affording a crude product, which was purified by typical silica gel column chromatography, eluting with petroleum ether/AcOEt (90:10) to give pure product (0.694 g, 81%) as colorless crystals. MS (ESI) m/z: 268 [M−Na]+. 1H NMR (CDCl3): δ 1.13 (t, J=7.2 Hz, 3H), 1.47 (s, 9H), 2.57-2.87 (m, 2H), 3.82 (s, 3H), 5.07 (d, J=7.1 Hz, 1H), 5.73 (d, J=4.5 Hz, 1H).

1. customat −78° C.
2. customthe reaction mixture was quenched with saturated NH4Cl solution
3. extractionextracted with AcOEt (3×15 mL)
4. washThe organic layer was washed with H2O and brine
5. dry with materialdried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customaffording a crude product, which
9. customwas purified by typical silica gel column chromatography
10. washeluting with petroleum ether/AcOEt (90:10)

ORD record

ord-0fbcf0b0a8b349b98a3ba84547cfcff1

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09353075B2