1,2-Diaminocyclohexane → 3-[4-(4-Chlorophenoxy)phenyl]-4-(3-methoxyphenyl)-oxazolidin-2-one

HRID 1972254Notes

Reaction equation

HRID 1972254 reaction equation
C(O[C:9](=[O:22])[NH:10][CH:11]([C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=1)[CH2:12][OH:13])C1C=CC=CC=1.[Cl:23][C:24]1[CH:37]=[CH:36][C:27]([O:28][C:29]2[CH:34]=[CH:33][C:32](I)=[CH:31][CH:30]=2)=[CH:26][CH:25]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C1(N)CCCCC1N>[Cu]I.CN(C=O)C>[Cl:23][C:24]1[CH:37]=[CH:36][C:27]([O:28][C:29]2[CH:34]=[CH:33][C:32]([N:10]3[CH:11]([C:14]4[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=4)[CH2:12][O:13][C:9]3=[O:22])=[CH:31][CH:30]=2)=[CH:26][CH:25]=1

Participants

7

Reactant 4

HCID 46101,2-DiaminocyclohexaneHCID 62657Potassium Phosphate, TribasicHCID 193519901-Chloro-4-(4-iodophenoxy)benzeneHCID 68702649benzyl N-[2-hydroxy-1-(3-methoxyphenyl)ethyl]carbamate

Product 1

HCID 687060693-[4-(4-Chlorophenoxy)phenyl]-4-(3-methoxyphenyl)-oxazolidin-2-oneYield 76.8%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

To a dry round bottom flask is added [2-hydroxy-1-(3-methoxy-phenyl)ethyl]-carbamic acid benzyl ester (300 mg, 1 mmol), 1-(4-chlorophenoxy)-4-iodobenzene (330 mg, 1 mmol), K3PO4 (210 mg), 1,2-cyclohexanediamine (15 μL) and CuI (20 mg), and DMF (5 mL). The mixture is evacuated and back-filled with nitrogen three times. The reaction mixture is heated to 110° C. for 7 h. The reaction is then cooled to room temperature, diluted with EtOAc (50 mL), washed with 1N HCl, and brine, subsequently dried over MgSO4, filtered, and concentrated to give the crude product, which is purified by flash chromatography on silica gel (EtOAc/Hex: 1/2) to provide 3-[4-(4-chlorophenoxy)phenyl]-4-(3-methoxyphenyl)-oxazolidin-2-one (304 mg).

Workup

  1. customThe mixture is evacuated
  2. additionback-filled with nitrogen three times
  3. temperatureThe reaction is then cooled to room temperature
  4. additiondiluted with EtOAc (50 mL)
  5. washwashed with 1N HCl, and brine
  6. dry with materialsubsequently dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give the crude product, which
  10. customis purified by flash chromatography on silica gel (EtOAc/Hex: 1/2)

Sources & evidence

ORD record
ord-cf706bf919a247b6a5484cd9716f50ea
Source dataset
uspto-grants-2013_04
Patent number
US08431607B2

Reaction notes

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