tert-Butanol → HCID 90090780, compound

HRID 2178578Notes

Reaction equation

HRID 2178578 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:8]=[CH:7][N:6]2[C:9]([CH3:15])=[C:10](C([O-])=O)[N:11]=[C:5]2[CH:4]=1.C([N:20]([CH2:23]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:32])C=CC=CC=1.[C:42]([OH:46])([CH3:45])([CH3:44])[CH3:43]>>[F:17][C:2]([F:1])([F:16])[C:3]1[CH:8]=[CH:7][N:6]2[C:9]([CH3:15])=[C:10]([NH:20][C:23](=[O:32])[O:46][C:42]([CH3:45])([CH3:44])[CH3:43])[N:11]=[C:5]2[CH:4]=1

Participants

5

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 131731118HCID 131731118, compound

Product 1

HCID 90090780HCID 90090780, compoundYield 40%

Procedure

To a solution of compound 17-B (0.860 g, 3.52 mmol) in tert-butanol (20 mL) and triethylamine (1.07 g, 10.57 mmol) was added diphenylphosphoryl azide (0.969 g, 3.52 mmol) and the reaction mixture was heated at reflux temperature for 6 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 17-C as a light yellow solid (0.447 g, 40%); MS m/z (M+H+) 316.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux temperature for 6 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-b1dce9e8f86346d1a8a06e97d73dc1d4
Source dataset
uspto-grants-2015_06
Patent number
US09067935B2

Reaction notes

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