Methanol → Acetamide, N-[[(5S)-3-[3-fluoro-4-(1-oxido-4-thiomorpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]-

HRID 2294080Notes

Reaction equation

HRID 2294080 reaction equation
I([O-])(=O)(=O)=O.[Na+].[F:7][C:8]1[CH:9]=[C:10]([N:20]2[CH2:24][CH:23]([CH2:25][NH:26][C:27](=[O:29])[CH3:28])[O:22][C:21]2=[O:30])[CH:11]=[CH:12][C:13]=1[N:14]1[CH2:19][CH2:18][S:17][CH2:16][CH2:15]1.C[OH:32]>O>[F:7][C:8]1[CH:9]=[C:10]([N:20]2[CH2:24][C@H:23]([CH2:25][NH:26][C:27](=[O:29])[CH3:28])[O:22][C:21]2=[O:30])[CH:11]=[CH:12][C:13]=1[N:14]1[CH2:15][CH2:16][S:17](=[O:32])[CH2:18][CH2:19]1

Participants

5

Reactant 3

HCID 887MethanolHCID 18535983HCID 18535983, compoundHCID 23667635Sodium periodate

Product 1

HCID 465952Acetamide, N-[[(5S)-3-[3-fluoro-4-(1-oxido-4-thiomorpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

Sodium metaperiodate (42 mg, 0.196 mmol) was dissolved in water (1 mL) and then cooled to 0° C. (ice bath). Next, the N-[[3-[3-fluoro-4-(4-thiomorpholinyl) phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide (66 mg, 0.187 mmol) was added. Methanol (3 mL) was added to increase solubility. The reaction was stirred at 0° C. for an additional 4 hours under N2 before being stoppered and stored in the freezer (65 hours). The reaction was filtered through a medium-porosity sintered glass funnel, rinsing the flask and filter cake with CHCl3 (5 mL). The filtrate was transferred to a separatory funnel, the layers separated, and the water layer further extracted with more CHCl3 (3×5 mL). The organic layers were combined, dried over anhydrous Na2SO4, filtered and then concentrated under reduced pressure to yield 80 mg of a gummy solid. The material was chromatographed on silica gel (10 g silica, packed with 10% CH3CN/CHCl3), eluting with a gradient of 1-5% MeOH in 10% CH3CN/CHCl3 to give 49 mg (71%) of the title compound as an off-white solid with amp of 159°-161° C. and a HRMS (M+) calculated for C16H20N3O4FS 369.1158, found 369.1182.

Workup

  1. temperatureto increase solubility
  2. customstored in the freezer (65 hours)
  3. filtrationThe reaction was filtered through a medium-porosity sintered glass funnel
  4. washrinsing the flask
  5. filtrationfilter cake with CHCl3 (5 mL)
  6. customThe filtrate was transferred to a separatory funnel
  7. customthe layers separated
  8. extractionthe water layer further extracted with more CHCl3 (3×5 mL)
  9. dry with materialdried over anhydrous Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bb1e3c0e63284a70b7af705a92ea419f
Source dataset
uspto-grants-1997_11
Patent number
US05688792

Reaction notes

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