Water → HCID 11307550, compound

HRID 915292Notes

Reaction equation

HRID 915292 reaction equation
Cl[CH2:2][O:3][C:4](=[O:31])[N:5]([C:28](=[O:30])[CH3:29])[CH2:6][C@@H:7]1[O:11][C:10](=[O:12])[N:9]([C:13]2[CH:18]=[CH:17][C:16]([CH:19]3[CH2:24][CH2:23][S:22](=[O:26])(=[O:25])[CH2:21][CH2:20]3)=[C:15]([F:27])[CH:14]=2)[CH2:8]1.[C:32]([O-:40])(=[O:39])[C:33]1[CH:38]=[CH:37][N:36]=[CH:35][CH:34]=1.[Cs+].[I-].[Na+].O>C(#N)C>[C:28]([N:5]([CH2:6][C@@H:7]1[O:11][C:10](=[O:12])[N:9]([C:13]2[CH:18]=[CH:17][C:16]([CH:19]3[CH2:24][CH2:23][S:22](=[O:26])(=[O:25])[CH2:21][CH2:20]3)=[C:15]([F:27])[CH:14]=2)[CH2:8]1)[C:4]([O:3][CH2:2][O:40][C:32](=[O:39])[C:33]1[CH:38]=[CH:37][N:36]=[CH:35][CH:34]=1)=[O:31])(=[O:30])[CH3:29]

Participants

6

Reactant 4

HCID 962WaterHCID 5238Sodium IodideHCID 23698454HCID 23698454, compoundHCID 58958555HCID 58958555, compound

Product 1

HCID 11307550HCID 11307550, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(R)-acetyl-{3-[4-(1,1-dioxo-hexahydro-1λ6-thiopyran-4-yl)-3-fluoro-phenyl]-2-oxo-oxazolidin-5-ylmethyl}-carbamic acid chloromethyl ester (10) (0.40 g, 0.84 mmol), cesium isonicotinate (0.33 g, 1.301 mmol) and sodium iodide (0.13 g, 0.86 mmol) in 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 (0-5% MeOH over 1 hour and 20 minutes) to afford the title compound. Isolated yield: 80%. 1H NMR (400 MHz, DMSO-d6): δ 8.78 (d, 2H), 7.82 (d, 2H), 7.36 (d, 1H), 7.30 (t, 1H), 7.18 (d, 1H), 6.02 (dd, 2H), 4.76-4.70 (m, 1H), 4.10-4.05 (m, 2H), 3.89-3.85 (m, 1H), 3.77-3.74 (m, 1H), 3.35-3.26 (m, partially obscured by water, 2H), 3.19-3.11 (m, 1H), 3.07-3.04 (m, 2H), 2.43 (d, partially obscured by DMSO, 3H), 2.11 (q, 2H), 2.01-1.97 (m, 2H); MS-APCI (m/z+): 341, 564.

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 (0-5% MeOH over 1 hour and 20 minutes)

Sources & evidence

ORD record
ord-55526458ab804b0184989ca1c896aa6b
Source dataset
uspto-grants-2007_09
Patent number
US07265140B2

Reaction notes

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