Dichloromethane → HCID 178445743, compound

HRID 1036416Notes

Reaction equation

HRID 1036416 reaction equation
[C:1]([O:5][C:6](=[O:37])[NH:7][C:8]1([C:16]2[CH:25]=[CH:24][C:23]3[C:18](=[CH:19][CH:20]=[C:21]([O:26][C@H:27]4[CH2:32][CH2:31][C@@H:30]([CH2:33][CH2:34][CH2:35][CH3:36])[CH2:29][CH2:28]4)[CH:22]=3)[CH:17]=2)[CH2:13][O:12][C:11]([CH3:15])([CH3:14])[O:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[I:38]N1C(=O)CCC1=O.C(Cl)Cl>[Cl-].[Cl-].[Cl-].[Cl-].[Zr+4]>[C:1]([O:5][C:6](=[O:37])[NH:7][C:8]1([C:16]2[CH:25]=[CH:24][C:23]3[C:18](=[CH:19][CH:20]=[C:21]([O:26][C@H:27]4[CH2:32][CH2:31][C@@H:30]([CH2:33][CH2:34][CH2:35][CH3:36])[CH2:29][CH2:28]4)[C:22]=3[I:38])[CH:17]=2)[CH2:13][O:12][C:11]([CH3:15])([CH3:14])[O:10][CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 120273N-IodosuccinimideHCID 178445742HCID 178445742, compound

Product 1

HCID 178445743HCID 178445743, compound

Reagents, catalysts & solvents 1

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

Procedure

A solution of {5-[6-(cis-4-butylcyclohexyloxy)-naphthalen-2-yl]-2,2-dimethyl-1,3-dioxinan-5-yl}-carbamic acid tert-butyl ester (0.101 g, 0.000197 mol) and N-iodosuccinimide (56 mg, 0.00025 mol, Acros) in methylene chloride (3.0 mL, 0.047 mol, Acros) was stirred at room temperature under an atmosphere of Argon. To this was added zirconium tetrachloride (14 mg, 0.000060 mol, Strem). After 5 min, the reaction mixture was evaporated then diluted with methylene chloride, silica gel was added and the solvent was evaporated. The material was purified by silica gel chromatography to give the product in 111 mg yield (88%).

Workup

  1. customthe reaction mixture was evaporated
  2. additionthen diluted with methylene chloride, silica gel
  3. additionwas added
  4. customthe solvent was evaporated
  5. customThe material was purified by silica gel chromatography
  6. customto give the product in 111 mg
  7. customyield (88%)

Sources & evidence

ORD record
ord-4f3a6d27bd3c4caaa846d6b25ee274d1
Source dataset
uspto-grants-2013_10
Patent number
US08546359B2

Reaction notes

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