Potassium Carbonate → HCID 178490676, compound

HRID 78539

Reaction equation

HRID 78539 reaction equation
[C:1]([C:5]1[S:9][C:8]([NH:10][C:11](=[O:21])[C:12]2[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=2[O:19][CH3:20])=[N:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].CC1C=CC(S(O[CH2:33][C@@H:34]2[CH2:38][O:37][C:36](=[O:39])[NH:35]2)(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.[I-].C([N+](CC)(CC)CC)C.C1(C)C=CC=CC=1>[C:1]([C:5]1[S:9]/[C:8](=[N:10]\[C:11](=[O:21])[C:12]2[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=2[O:19][CH3:20])/[N:7]([CH2:33][C@H:34]2[CH2:38][O:37][C:36](=[O:39])[NH:35]2)[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 11032956(S)-(2-oxooxazolidin-4-yl)methyl 4-methylbenzenesulfonateHCID 87094486n-(5-Tert-butylthiazol-2-yl)-5-chloro-2-methoxybenzamide

Product 1

HCID 178490676HCID 178490676, compoundYield 42.9%

Reagents, catalysts & solvents 4

HCID 6225Tetraethylammonium IodideCatalystHCID 67553Tetrabutylammonium IodideCatalystHCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 1140TolueneSolvent

Procedure

A mixture of Example 244A (180 mg, 0.55 mmol), (S)-(2-oxo-oxazolidin-4-yl)methyl 4-methylbenzenesulfonate (180 mg, 0.67 mmol), potassium carbonate (153 mg, 1.1 mmol), tetrabutylammonium iodide (10 mg, 0.03 mmol), tetrabutylammonium hydrogen sulfate (10 mg, 0.03 mmol) and tetraethylammonium iodide (10 mg, 0.04 mmol) in toluene (35 mL) was refluxed for 14 h. The mixture was washed with water, brine, dried with MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by chromatography over silica gel (EtOAc as eluent) to afford 100 mg of the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 1.36 (s, 9H), 3.92 (s, 3H), 4.11-4.26 (m, 2H), 4.30-4.41 (m, 2H), 4.57 (t, J=8.6 Hz, 1H), 6.33 (s, 1H), 6.62 (s, 1H), 6.93 (d, J=8.8 Hz, 1H), 7.35 (dd, J=9.0, 2.9 Hz, 1H), 7.79 (d, J=2.7 Hz, 1H). MS (DCI/NH3) m/z 424 (M+H)+.

Workup

  1. washThe mixture was washed with water, brine
  2. dry with materialdried with MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by chromatography over silica gel (EtOAc as eluent)

Sources & evidence

ORD record
ord-b5210208848d4ae0aced843378dcc55f
Source dataset
uspto-grants-2014_09
Patent number
US08841334B2

Linked notes

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