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Dichloromethane → HCID 178445736, compound

HRID 1036503
Notes
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Reaction equation

HRID 1036503 reaction equation
[C:1]([CH:5]1[CH2:10][CH2:9][CH: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.[F:32]N(S(C1C=CC=CC=1)(=O)=O)S(C1C=CC=CC=1)(=O)=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]([F: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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 588007N-FluorobenzenesulfonimideHCID 67414115(R)-4-[6-(4-tert-Butylcyclohexyloxy)naphthalen-2-yl]-4-methyl-oxazolidin-2-one

Product 1

HCID 178445736HCID 178445736, compoundYield 42%

Reagents, catalysts & solvents 1

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

Conditions

Temperature
40 °C

Procedure

(R)-4-[6-(4-tert-Butyl-cyclohexyloxy)-naphthalen-2-yl]-4-methyl-oxazolidin-2-one (0.3012 g, 0.0007895 mol) was dissolved in methylene chloride (5.00 mL, 0.0780 mol) in a capped 40 mL vial equipped with a magnetic stir bar. N-fluoro-N-(phenylsulfonyl)benzenesulfonamide (0.249 g, 0.000789 mol) was added followed by zirconium tetrachloride (0.184 g, 0.000789 mol) and the mixture was heated overnight at 40° C. The reaction mixture was cooled to room temperature then concentrated to dryness under reduced pressure, adsorbed onto silica gel and purified by flash chromatography (0-55% EtOAc in hexanes) to give 131.3 mg of the title compound (42% yield).

Workup

  1. customvial equipped with a magnetic stir bar
  2. temperatureThe reaction mixture was cooled to room temperature
  3. concentrationthen concentrated to dryness under reduced pressure
  4. custompurified by flash chromatography (0-55% EtOAc in hexanes)

Sources & evidence

ORD record
ord-f698c23f4a2947fbb83c69a07156e9e5
Source dataset
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08546359B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes