Acetone → HCID 86682291, compound

Temperature

0 °C

To a round bottom flask were added 10 mL DCM and (S)-4-benzyl-3-(2-(3-bromo-4-methoxyphenyl)acetyl)oxazolidin-2-one (1.0 g, 2.47 mmol). TiCl4 (2.6 mL, 2.60 mmol, 1M DCM solution) was added at 0° C. After stirring at 0° C. for 5 mins, DIEA (0.45 mL, 2.6 mmol) was added via syringe. The reaction mixture was stirred at 0° C. for 30 mins. Acetone (0.27 mL, 3.71 mmol) was added followed by more of TiCl4 (2.6 mL, 2.6 mmol, 1 M DCM solution). The reaction mixture was stirred at 0° C. for 2 hrs. It was quenched by addition of 80 mL sat. NH4Cl aqueous solution. The resulting reaction mixture was extracted with 120 mL EtOAc/hexane (1:1). Organics were dried over sodium sulfate, filtered and concentrated. Crude product was purified on Combiflash prepacked silica gel column, eluted with 5% to 40% EtOAc in hexane to give 1.1 g desired product as viscous material. 1H NMR (500 MHz, CDCl3): δ 7.70 (s, 1H), 7.1-7.4 (m, 6H), 6.88 (d, J=8.5 Hz, 1H), 4.68 (m, 1H), 4.1 (m, 2H), 3.93 (s, 3H), 3.83 (s, 1H), 3.43 (dd, J=3.4, 13.3 Hz, 1H), 2.82 (dd, J=9.9, 13.3 Hz, 1H), 1.46 (s, 3H), 1.09 (s, 3H).

1. stirringThe reaction mixture was stirred at 0° C. for 30 mins
2. stirringThe reaction mixture was stirred at 0° C. for 2 hrs
3. customIt was quenched by addition of 80 mL sat. NH4Cl aqueous solution
4. customThe resulting reaction mixture
5. extractionwas extracted with 120 mL EtOAc/hexane (1:1)
6. dry with materialOrganics were dried over sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated
9. customCrude product was purified on Combiflash prepacked silica gel column
10. washeluted with 5% to 40% EtOAc in hexane

ORD record

ord-de2c8ae121914d3dada4616a8a806d21

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08871738B2