Triacetoxyperiodinane → 2-chloro-N-(4-(5-phenyloxazol-2-yl)phenyl)benzamide

HRID 1951599Notes

Reaction equation

HRID 1951599 reaction equation
[Cl:1][C:2]1[CH:28]=[CH:27][CH:26]=[CH:25][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([NH:15][CH2:16][CH:17]([OH:24])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=O)=[CH:9][CH:8]=1)=[O:5].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.S(=O)(=O)(O)[O-].[Na+]>CN(C=O)C.C(OCC)(=O)C>[Cl:1][C:2]1[CH:28]=[CH:27][CH:26]=[CH:25][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[O:24][C:17]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)=[CH:16][N:15]=2)=[CH:9][CH:8]=1)=[O:5]

Participants

6

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 516919Sodium BisulfateHCID 574653822-chloro-N-(4-(((2-hydroxy-2-phenylethyl)amino)carbonyl)phenyl)benzamide

Product 1

HCID 445490042-chloro-N-(4-(5-phenyloxazol-2-yl)phenyl)benzamideYield 168.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

under an N2 atmosphere, 2-chloro-N-(4-(((2-hydroxy-2-phenylethyl)amino)carbonyl)phenyl)benzamide (0.578 g, 1.46 mmol) was dissolved in DMF (7.00 ml). Dess-Martin periodinane (0.745 g, 1.76 mmol) was added and the reaction was stirred at room temperature for 3 hours. The reaction was diluted with ethyl acetate and a saturated aqueous solution of sodium bisulfate. The layers were separated and the organic layer was washed with water and brine. The organic layer was dried (Na2SO4), filtered and concentrated in vacuo. The residue was triturated with ethyl acetate and hexanes. The resulting solid was collected by filtration. The solid was suspended in pyridine (8.00 ml) and POCl3 (4.00 ml). The reaction was heated to 70° C. for 3 hours. The reaction was poured into a cooled 5% NaHCO3 solution and stirred vigorously for 15 minutes. The mixture was then extracted with ethyl acetate. The organic layer was dried (Na2SO4), filtered and concentrated in vacuo. The crude residue was purified by column chromatography eluting with 25% to 50% ethyl acetate in hexanes. The resulting solid was triturated with ethyl acetate/hexanes and collected by filtration to afford 2-chloro-N-(4-(5-phenyloxazol-2-yl)phenyl)benzamide (0.920 g, 16.8%). ESI m/z=375.0 (M+H+).

Workup

  1. customThe layers were separated
  2. washthe organic layer was washed with water and brine
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was triturated with ethyl acetate and hexanes
  7. filtrationThe resulting solid was collected by filtration
  8. temperatureThe reaction was heated to 70° C. for 3 hours
  9. additionThe reaction was poured into a cooled 5% NaHCO3 solution
  10. stirringstirred vigorously for 15 minutes
  11. extractionThe mixture was then extracted with ethyl acetate
  12. dry with materialThe organic layer was dried (Na2SO4)
  13. filtrationfiltered
  14. concentrationconcentrated in vacuo
  15. customThe crude residue was purified by column chromatography
  16. washeluting with 25% to 50% ethyl acetate in hexanes
  17. customThe resulting solid was triturated with ethyl acetate/hexanes
  18. filtrationcollected by filtration

Sources & evidence

ORD record
ord-2e85ecb0498e4df8b0c5c6448d135bc3
Source dataset
uspto-grants-2013_03
Patent number
US08404722B2

Reaction notes

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