N-Iodosuccinimide → HCID 178444566, compound

HRID 2389057Notes

Reaction equation

HRID 2389057 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-dimethylpropyl)-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-08a323a41e1f4938828f1cd2e529864f
Source dataset
uspto-grants-2012_09
Patent number
US08269043B2

Reaction notes

Loading…