N-Iodosuccinimide → HCID 178421580, compound

HRID 1036518Notes

Reaction equation

HRID 1036518 reaction equation
[I:1]N1C(=O)CCC1=O.[CH3:9][C@@:10]1([C:16]2[CH:25]=[CH:24][C:23]3[C:18](=[CH:19][CH:20]=[C:21]([O:26][C@H:27]4[CH2:32][CH2:31][C@H:30]([C:33]([F:36])([F:35])[F:34])[CH2:29][CH2:28]4)[CH:22]=3)[CH:17]=2)[CH2:14][O:13][C:12](=[O:15])[NH:11]1>C(Cl)Cl.[Cl-].[Cl-].[Cl-].[Cl-].[Zr+4]>[I:1][C:22]1[C:21]([O:26][C@H:27]2[CH2:28][CH2:29][C@H:30]([C:33]([F:36])([F:34])[F:35])[CH2:31][CH2:32]2)=[CH:20][CH:19]=[C:18]2[C:23]=1[CH:24]=[CH:25][C:16]([C@:10]1([CH3:9])[CH2:14][O:13][C:12](=[O:15])[NH:11]1)=[CH:17]2

Participants

5

Reactant 2

HCID 120273N-IodosuccinimideHCID 178421576HCID 178421576, compound

Product 1

HCID 178421580HCID 178421580, compound

Reagents, catalysts & solvents 2

HCID 9856075Zirconium chloride (ZrCl4), (T-4)-CatalystHCID 6344DichloromethaneSolvent

Procedure

N-Iodosuccinimide (588 mg, 0.00261 mol, Acros) and zirconium tetrachloride (98 mg, 0.00042 mol, Strem) was added to a solution of repurified (R)-4-methyl-4-[6-(trans-4-trifluoromethyl-cyclohexyloxy)-naphthalen-2-yl]-oxazolidin-2-one (786 mg, 0.00200 mol) in methylene chloride (30 mL, Acros) and were stirred at room temperature for 30 min. Silica gel was added and the reaction was evaporated to dryness. The residue was purified by silica gel chromatography using 0-100% ethyl acetate in hexanes as eluent. Cis and trans isomers were fully resolved and isolated was 822 mg (79%) of pure trans product (Rf=0.31 in 1:1 hexanes/ethyl acetate).

Workup

  1. additionSilica gel was added
  2. customthe reaction was evaporated to dryness
  3. customThe residue was purified by silica gel chromatography
  4. customisolated

Sources & evidence

ORD record
ord-6165f7d87dcb4e1db7bb44f9dfa181a7
Source dataset
uspto-grants-2013_10
Patent number
US08546359B2

Reaction notes

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