Dichloromethane → HCID 178445737, compound

HRID 1036413Notes

Reaction equation

HRID 1036413 reaction equation
[C:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]([O:11][C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[CH:18]=[C:17]([C@:22]2([CH3:28])[CH2:26][O:25][C:24](=[O:27])[NH:23]2)[CH:16]=[CH:15]3)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].C(Cl)Cl.[I:32]N1C(=O)CCC1=O>[Cl-].[Cl-].[Cl-].[Cl-].[Zr+4]>[C:1]([C@H:5]1[CH2:6][CH2:7][C@H:8]([O:11][C:12]2[C:13]([I:32])=[C:14]3[C:19](=[CH:20][CH:21]=2)[CH:18]=[C:17]([C@:22]2([CH3:28])[CH2:26][O:25][C:24](=[O:27])[NH:23]2)[CH:16]=[CH:15]3)[CH2:9][CH2:10]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 120273N-IodosuccinimideHCID 178445731HCID 178445731, compound

Product 1

HCID 178445737HCID 178445737, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 9856075Zirconium chloride (ZrCl4), (T-4)-Catalyst

Procedure

(R)-4-[6-(trans-4-tert-Butylcyclohexyloxy)naphthalen-2-yl]-4-methyl-oxazolidin-2-one (0.4719 g, 0.001237 mol) was dissolved in methylene chloride (5.00 mL, 0.0780 mol) in a 40 mL vial. N-Iodosuccinimide (0.312 g, 0.00138 mol) and zirconium tetrachloride (0.043 g, 0.00018 mol) were added and the mixture was stirred at room temperature. After 3 hours the reaction was complete. The mixture was adsorbed onto silica and purified by flash is chromatography (0-60% EtOAc in hexanes) to give 0.112 g of the title compound (42% yield).

Workup

  1. custompurified by flash

Sources & evidence

ORD record
ord-ba2c448d012b4fe8a7acbb49eb72912e
Source dataset
uspto-grants-2013_10
Patent number
US08546359B2

Reaction notes

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