Dimethyl Sulfide → (R)-4-((R)-4-Benzyl-2-oxo-oxazolidin-3-yl)-3-(3,5-dichloro-4'-fluoro-biphenyl-4-ylmethyl)-4-oxo-butyraldehyde

온도

-78 °C

Dissolve (R)-4-Benzyl-3-[(S)-2-(3,5-dichloro-4′-fluoro-biphenyl-4-ylmethyl)-pent-4-enoyl]-oxazolidin-2-one (1.95 mmoles; 1.00 g) in dichloromethane (10 ml) and methanol (1 mL). Cool the mixture to −78° C. in a dry ice acetone bath and add ozone subsurface to the reaction with an exotherm to −71° C. The reaction turns blue, and then sweep with nitrogen to a clear color. Add dimethyl sulfide (2 mL; 27.20 mmoles) dropwise at −78° C. Warm the solution to ambient temperature and then test with KI starch paper (test is negative). Remove the solvents under vacuum, extract with MTBE, wash with pH=7 buffer, water, and brine. Concentrate the organics under vacuum to give a white non-crystalline solid (0.81 g). LCMS (M+1=515.39).

1. customto the reaction with an exotherm to −71° C
2. customdropwise at −78° C
3. temperatureWarm the solution to ambient temperature
4. customRemove the solvents under vacuum
5. extractionextract with MTBE
6. washwash with pH=7 buffer
7. concentrationConcentrate the organics under vacuum

ORD 기록

ord-89e1a09db3e344e2b38cfa7c89e9f50c

출처 데이터셋

uspto-grants-2011_07

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US07981918B2