tert-Butanol → HCID 67966899, compound

HRID 1916867Notes

Reaction equation

HRID 1916867 reaction equation
[CH2:1]([C:3]1[N:7]2[CH:8]=[CH:9][CH:10]=[C:11]([C:12]([F:15])([F:14])[F:13])[C:6]2=[N:5][C:4]=1C([O-])=O)[CH3:2].C([N:21]([CH2:24]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:33])C=CC=CC=1.[C:43]([OH:47])([CH3:46])([CH3:45])[CH3:44]>>[CH2:1]([C:3]1[N:7]2[CH:8]=[CH:9][CH:10]=[C:11]([C:12]([F:13])([F:14])[F:15])[C:6]2=[N:5][C:4]=1[NH:21][C:24](=[O:33])[O:47][C:43]([CH3:46])([CH3:45])[CH3:44])[CH3:2]

Participants

5

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 131731117HCID 131731117, compound

Product 1

HCID 67966899HCID 67966899, compoundYield 57%

Procedure

To a solution of compound 13-B (0.620 g, 2.40 mmol) in tert-butanol (10 mL) and triethylamine (0.733 g, 7.2 mmol) was added diphenylphosphoryl azide (0.658 g, 2.4 mmol) and the reaction mixture was heated at reflux temperature for 7 h. The solvent was removed in vacuo and ethyl acetate was added. The organic layer was washed with 1M sodium carbonate solution, dried over sodium sulfate, and the solvent removed in vacuo. The resulting residue was purified by flash column chromatography, eluting with a hexanes-EtOAc gradient to give compound 13-C (0.450 g, 57%); MS m/z (M+H+) 330.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux temperature for 7 h
  3. customThe solvent was removed in vacuo and ethyl acetate
  4. additionwas added
  5. washThe organic layer was washed with 1M sodium carbonate solution
  6. dry with materialdried over sodium sulfate
  7. customthe solvent removed in vacuo
  8. customThe resulting residue was purified by flash column chromatography
  9. washeluting with a hexanes-EtOAc gradient

Sources & evidence

ORD record
ord-f1d2037d95bd4610884bdffdb112040e
Source dataset
uspto-grants-2013_12
Patent number
US08618150B2

Reaction notes

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