tert-Butanol → HCID 67966892, compound

HRID 1916865Notes

Reaction equation

HRID 1916865 reaction equation
[CH:1]1([C:4]2[N:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:7]3=[N:6][C:5]=2C(O)=O)[CH2:3][CH2:2]1.C([N:18]([CH2:21]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:30])C=CC=CC=1.[C:40]([OH:44])([CH3:43])([CH3:42])[CH3:41]>>[CH:1]1([C:4]2[N:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:7]3=[N:6][C:5]=2[NH:18][C:21](=[O:30])[O:44][C:40]([CH3:43])([CH3:42])[CH3:41])[CH2:2][CH2:3]1

Participants

5

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 67954049HCID 67954049, compound

Product 1

HCID 67966892HCID 67966892, compound

Procedure

To a solution of compound 12-C (0.841 g, 4.16 mmol) in tert-butanol (17 mL) and triethylamine (1.27 g, 12.48 mmol) was added diphenylphosphoryl azide (1.14 g, 4.16 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 12-D (0.171 g, 15%); MS m/z (M+H+) 274.

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
  10. customto give compound 12-D (0.171 g, 15%)

Sources & evidence

ORD record
ord-def35cc5128c41898b4a7f5a34507eb9
Source dataset
uspto-grants-2013_12
Patent number
US08618150B2

Reaction notes

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