HCID 10494560, compound → HCID 69364244, compound

HRID 723768Notes

Reaction equation

HRID 723768 reaction equation
[N:1]1([C:6]2[CH:11]=[CH:10][C:9]([N:12]3[CH2:16][C@H:15]([CH2:17][N:18]=[N+:19]=[N-:20])[O:14][C:13]3=[O:21])=[CH:8][C:7]=2[F:22])[CH:5]=[CH:4][N:3]=[CH:2]1.[C:23]12CC(CC1)=C[CH:24]=2>O1CCOCC1>[N:1]1([C:6]2[CH:11]=[CH:10][C:9]([N:12]3[CH2:16][C@H:15]([CH2:17][N:18]4[CH:24]=[CH:23][N:20]=[N:19]4)[O:14][C:13]3=[O:21])=[CH:8][C:7]=2[F:22])[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

4

Reactant 2

HCID 10494560HCID 10494560, compoundHCID 18006658Norborna-diene

Product 1

HCID 69364244HCID 69364244, compoundYield 80.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

(5R)-3-(4-Imidazol-1-yl-3-fluorophenyl)-5-azidomethyloxazolidin-2-one (755 mg, 1.35 mM) was dissolved in dioxane (40 ml), treated with norbornadiene (115 g, 12.5 mM) and heated under reflux for 16 hours. After removal of the solvent, the residue was dissolved in the minimum of dichloromethane and purified by chromatography on a 20 g silica Mega Bond Elut® column, eluting with a gradient increasing in polarity from 0 to 10% methanol in dichloromethane. Relevant fractions were combined and evaporated to give the desired product (660 mg).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 16 hours
  3. customAfter removal of the solvent
  4. dissolutionthe residue was dissolved in the minimum of dichloromethane
  5. custompurified by chromatography on a 20 g silica Mega Bond Elut® column
  6. washeluting with a gradient
  7. temperatureincreasing in polarity from 0 to 10% methanol in dichloromethane
  8. customevaporated

Sources & evidence

ORD record
ord-c95a40b4119c43b8a860311c17cd8ce5
Source dataset
uspto-grants-2006_11
Patent number
US07141583B2

Reaction notes

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