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

HRID 1013833Notes

Reaction equation

[CH2:1]([C@@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:35])[C@H:15]([CH2:19][C:20]1[C:25]([Cl:26])=[CH:24][C:23]([C:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=2)=[CH:22][C:21]=1[Cl:34])[CH2:16][CH:17]=C)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:36]=[O+][O-].CSC>ClCCl.CO>[CH2:1]([C@@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:35])[C@H:15]([CH2:19][C:20]1[C:25]([Cl:26])=[CH:24][C:23]([C:27]2[CH:28]=[CH:29][C:30]([F:33])=[CH:31][CH:32]=2)=[CH:22][C:21]=1[Cl:34])[CH2:16][CH:17]=[O:36])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: -78 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record: ord-89e1a09db3e344e2b38cfa7c89e9f50c
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07981918B2

Reaction notes

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