Dichloromethane → HCID 178421578, compound

HRID 2389054Notes

Reaction equation

HRID 2389054 reaction equation
[C: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)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[I:31]N1C(=O)CCC1=O.C(Cl)Cl>[Cl-].[Cl-].[Cl-].[Cl-].[Zr+4]>[C:1]1([C@H:7]2[CH2:12][CH2:11][C@H:10]([O:13][C:14]3[C:15]([I:31])=[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)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 120273N-IodosuccinimideHCID 178421571HCID 178421571, compound

Product 1

HCID 178421578HCID 178421578, compoundYield 86.3%

Reagents, catalysts & solvents 1

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

Procedure

A mixture of (R)-4-(6-(cis-4-phenyl-cyclohexyloxy)naphthalen-2-yl)-4-methyloxazolidin-2-one (Example 30, 71.4 mg 0.000178 mol), N-iodosuccinimide (44.8 mg, 0.000199 mol) and zirconium tetrachloride (6.2 mg, 0.000027 mol) in methylene chloride (1.46 mL, 0.0228 mol) was heated to reflux under Ar in a vial for 6 h. LCMS showed the reaction to be completed. The precipitate was filtered off and the residue was purified with Isco column eluted with EtOAc in hexane from 0 to 40% to give (R)-4-(6-(trans-4-phenyl-cyclohexyloxy)-5-iodonaphthalen-2-yl)-4-methyloxazolidin-2-one as a solid (81.0 mg, 86% yield). LCMS 528.27 ([M+1], 80%).

Workup

  1. temperaturewas heated
  2. temperatureto reflux under Ar in a vial for 6 h
  3. customthe reaction
  4. filtrationThe precipitate was filtered off
  5. customthe residue was purified with Isco column
  6. washeluted with EtOAc in hexane from 0 to 40%

Sources & evidence

ORD record
ord-c8b2d09e8b4f481ab014c74e6a6c2942
Source dataset
uspto-grants-2012_09
Patent number
US08269043B2

Reaction notes

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