Dichloromethane → HCID 178421579, compound

HRID 1036455Notes

Reaction equation

HRID 1036455 reaction equation
[CH:1]1([C@@H:7]2[CH2:12][CH2:11][C@H:10]([O:13][C:14]3[CH:15]=[C:16]4[C:21](=[CH:22][CH:23]=3)[CH:20]=[C:19]([C@:24]3([CH3:30])[CH2:28][O:27][C:26](=[O:29])[NH:25]3)[CH:18]=[CH:17]4)[CH2:9][CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(Cl)Cl.[I:34]N1C(=O)CCC1=O>[Cl-].[Cl-].[Cl-].[Cl-].[Zr+4]>[CH:1]1([C@@H:7]2[CH2:12][CH2:11][C@H:10]([O:13][C:14]3[C:15]([I:34])=[C:16]4[C:21](=[CH:22][CH:23]=3)[CH:20]=[C:19]([C@:24]3([CH3:30])[CH2:28][O:27][C:26](=[O:29])[NH:25]3)[CH:18]=[CH:17]4)[CH2:9][CH2:8]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 120273N-IodosuccinimideHCID 178421573HCID 178421573, compound

Product 1

HCID 178421579HCID 178421579, compoundYield 92,312.5%

Reagents, catalysts & solvents 1

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

Conditions

Temperature
23 °C

Procedure

To a solution of (R)-4-(6-(cis-4-cyclohexylcyclohexyloxy)naphthalen-2-yl)-4-methyloxazolidin-2-one (35.0 mg, 0.0000859 mol) in methylene chloride (2 mL, 0.03 mol), N-iodosuccinimide (38.6 mg, 0.000172 mol) was added, followed by zirconium tetrachloride (4.00 mg, 0.0000172 mol) at 23° C. The reaction mixture was then sonicated and stirred for 5 minutes at 23° C. TLC and LC/MS indicated a clean reaction. The majority of solvent was removed. Solid was removed via filtration through a Celite pad. The mixture was then loaded onto a column (SiO2, 4 g, 0-50% ethyl acetate/hexanes) to give a pure product (42.3 g, 92%).

Workup

  1. customThe reaction mixture was then sonicated
  2. customa clean reaction
  3. customThe majority of solvent was removed
  4. customSolid was removed via filtration through a Celite pad

Sources & evidence

ORD record
ord-9474e1d27ae746fb9e5f9b7092d3faef
Source dataset
uspto-grants-2013_10
Patent number
US08546359B2

Reaction notes

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