N-Iodosuccinimide → HCID 178444566, compound

HRID 1036397Notes

Reaction equation

HRID 1036397 reaction equation
[I:1]N1C(=O)CCC1=O.[CH3:9][C:10]([C@H:14]1[CH2:19][CH2:18][C@H:17]([O:20][C:21]2[CH:22]=[C:23]3[C:28](=[CH:29][CH:30]=2)[CH:27]=[C:26]([C@:31]2([CH3:37])[CH2:35][O:34][C:33](=[O:36])[NH:32]2)[CH:25]=[CH:24]3)[CH2:16][CH2:15]1)([CH3:13])[CH2:11][CH3:12]>C(Cl)Cl.[Cl-].[Cl-].[Cl-].[Cl-].[Zr+4]>[CH3:13][C:10]([C@H:14]1[CH2:19][CH2:18][C@H:17]([O:20][C:21]2[C:22]([I:1])=[C:23]3[C:28](=[CH:29][CH:30]=2)[CH:27]=[C:26]([C@:31]2([CH3:37])[CH2:35][O:34][C:33](=[O:36])[NH:32]2)[CH:25]=[CH:24]3)[CH2:16][CH2:15]1)([CH3:9])[CH2:11][CH3:12]

Participants

5

Reactant 2

HCID 120273N-IodosuccinimideHCID 178444564HCID 178444564, compound

Product 1

HCID 178444566HCID 178444566, compoundYield 25.3%

Reagents, catalysts & solvents 2

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

Procedure

A mixture of N-iodosuccinimide (204.77 mg, 0.91016 mmol), (R)-4-{6-[trans-4-(1,1-dimethyl-propyl)-cyclohexyloxy]-naphthalen-2-yl}-4-methyl-oxazolidin-2-one (300.00 mg, 0.75847 mmol) and zirconium tetrachloride (35.3 mg, 0.152 mmol) in methylene chloride (10.00 mL) was stirred RT for 2.5 hrs. LCMS showed the reaction was completed. The solution was purified with 4 g of silica gel column eluted with ethyl acetate in hexanes from 10 to 50% to give 100 mg of white precipitate, (R)-4-{6-[trans-4-(1,1-dimethyl-propyl)-cyclohexyloxy]-5-iodo-naphthalen-2-yl}-4-methyl-oxazolidin-2-one. (20% yield). MS: m/z=522.20 M+H.

Workup

  1. customThe solution was purified with 4 g of silica gel column
  2. washeluted with ethyl acetate in hexanes from 10 to 50%

Sources & evidence

ORD record
ord-be1b95b850184620a16dd18494f4c5ed
Source dataset
uspto-grants-2013_10
Patent number
US08546359B2

Reaction notes

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