Sodium Iodide → HCID 11192168, compound

HRID 915296Notes

Reaction equation

HRID 915296 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].[CH3:33][C:34]([CH3:39])([CH3:38])[C:35]([O-:37])=[O:36].[Cs+].[I-].[Na+].C(#N)C>O>[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:37][C:35](=[O:36])[C:34]([CH3:39])([CH3:38])[CH3:33])[CH3:3])=[O:32])(=[O:31])[CH3:30]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 6342AcetonitrileHCID 583616Cesium pivalateHCID 58958558HCID 58958558, compound

Product 1

HCID 11192168HCID 11192168, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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) (0.40 g, 0.81 mmol), cesium 2,2-dimethyl-propionate (0.38 g, 1.63 mmol), sodium iodide (0.121 g, 0.81 mmol) and acetonitrile (25 mL) are heated to 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 (0-4% MeOH over 1 hour and 30 minutes) to afford the title compound. Isolated yield: 30%. 1H NMR (400 MHz, DMSO-d6): δ 7.41-7.38 (m, 1H), 7.33 (t, 1H), 7.22 (dd, 1H), 6.71-6.65 (m, 1H), 4.77-4.68 (m, 1H), 4.12-3.94 (m, 2H), 3.88-3.74 (m, 2H), 3.36-3.28 (m, 2H), 3.18-3.12 (m, 1H), 3.07-3.03 (m, 2H), 2.37 (d, 3H), 2.15-2.06 (m, 2H), 2.00-1.97 (m, 2H) 1.44 (dd, 3H); 1.08 (d, 9H),

Workup

  1. temperatureto reflux overnight
  2. extractionthe reaction mixture is extracted with EtOAc
  3. washThe organic phases are washed separately with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. washeluting with MeOH/CH2Cl2 gradient (0-4% MeOH over 1 hour and 30 minutes)

Sources & evidence

ORD record
ord-890ad53733a24c87af3b302626f5a92b
Source dataset
uspto-grants-2007_09
Patent number
US07265140B2

Reaction notes

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