Water → HCID 11398414, compound

HRID 915293Notes

Reaction equation

HRID 915293 reaction equation
Cl[CH:2]([O:4][C:5](=[O:32])[N:6]([C:29](=[O:31])[CH3:30])[CH2:7][C@@H:8]1[O:12][C:11](=[O:13])[N:10]([C:14]2[CH:19]=[CH:18][C:17]([CH:20]3[CH2:25][CH2:24][S:23](=[O:27])(=[O:26])[CH2:22][CH2:21]3)=[C:16]([F:28])[CH:15]=2)[CH2:9]1)[CH3:3].[I-].[Na+].[C:35]([O-:39])(=[O:38])[CH2:36][CH3:37].[Cs+].O>C(#N)C>[C:29]([N:6]([CH2:7][C@@H:8]1[O:12][C:11](=[O:13])[N:10]([C:14]2[CH:19]=[CH:18][C:17]([CH:20]3[CH2:25][CH2:24][S:23](=[O:27])(=[O:26])[CH2:22][CH2:21]3)=[C:16]([F:28])[CH:15]=2)[CH2:9]1)[C:5]([O:4][CH:2]([O:39][C:35](=[O:38])[CH2:36][CH3:37])[CH3:3])=[O:32])(=[O:31])[CH3:30]

Participants

6

Reactant 4

HCID 962WaterHCID 5238Sodium IodideHCID 23693496Caesium propanoateHCID 58958558HCID 58958558, compound

Product 1

HCID 11398414HCID 11398414, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Acetyl-{3-[4-(1,1-dioxo-hexahydro-1λ6-thiopyran-4-yl)-3-fluoro-phenyl]-2-oxo-oxazolidin-5(R)-ylmethyl}-carbamic acid 1-chloro-ethyl ester (11) (0.20 g, 0.41 mmol) and sodium iodide (0.061 g, 0.41 mmol) are placed in acetonitrile (25 mL) and stirred at RT overnight. Cesium propionate (0.17 g, 0.82 mmol) is then added and the reaction is heated at reflux overnight. After cooling to RT, water is added and the reaction mixture is extracted with EtOAc and then with dichloromethane. The organic phases are washed separately with brine and then the organic layers are combined, dried over MgSO4, filtered, and conc in vacuo. The isolated residue is subjected to silica gel flash chromatography, eluting with MeOH/CH2Cl2 gradient (0-5% MeOH over 1 hour and 20 minutes) to afford the title compound. Isolated yield: 67%. 1H NMR (400 MHz, CDCl3): δ 7.48-7.42 (m, 1H), 7.21-7.17 (m, 1H), 7.13-7.10 (m, 1H), 6.90-6.85 (m, 1H), 4.83-4.69 (m, 1H), 4.14-3.98 (m, 3H), 3.73-3.64 (m, 1H), 3.13-3.04 (m, 5H), 2.52 (d, 3H), 2.48-2.31 (m, 3H), 2.29-2.13 (m, 2H), 1.56-1.51 (m, 4H), 1.15-1.07 (m, 3H).

Workup

  1. temperaturethe reaction is heated
  2. temperatureat reflux overnight
  3. temperatureAfter cooling to RT
  4. extractionthe reaction mixture is extracted with EtOAc
  5. washThe organic phases are washed separately with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. washeluting with MeOH/CH2Cl2 gradient (0-5% MeOH over 1 hour and 20 minutes)

Sources & evidence

ORD record
ord-4c802c4008ec45e38e8bac02292a5767
Source dataset
uspto-grants-2007_09
Patent number
US07265140B2

Reaction notes

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