Triethylamine → HCID 86604079, compound

HRID 1247018Notes

Reaction equation

HRID 1247018 reaction equation
O[C@H:2]([CH3:19])[CH2:3][N:4]1[C:18]2[C:11]3[N:12]=[C:13]([C:15]([NH2:17])=[O:16])[O:14][C:10]=3[CH:9]=[CH:8][C:7]=2[CH:6]=[N:5]1.C(N(CC)CC)C.CS(OS(C)(=O)=O)(=O)=O.[N-:36]=[N+:37]=[N-:38].[Na+]>O1CCCC1>[N:36]([C@@H:2]([CH3:19])[CH2:3][N:4]1[C:18]2[C:11]3[N:12]=[C:13]([C:15]([NH2:17])=[O:16])[O:14][C:10]=3[CH:9]=[CH:8][C:7]=2[CH:6]=[N:5]1)=[N+:37]=[N-:38]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 33557Sodium AzideHCID 81560Methanesulfonic anhydrideHCID 69587602HCID 69587602, compound

Product 1

HCID 86604079HCID 86604079, compoundYield 18.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
90 °C

Procedure

To a suspension of the product from Step D (0.90 g, 3.45 mmol) in tetrahydrofuran (20 mL) was added triethylamine (1.93 mL, 13.9 mmol); this mixture was cooled (ice bath), methane sulfonic anhydride (1.20 g, 6.92 mmol) was added, and the mixture was stirred for 20 minutes. Sodium azide (2.25 g, 34.6 mmol) was added and the mixture was evaporated to a residue which dissolved in dimethyl sulfoxide (20 mL) and heated at 90° C. for 2.5 hours. The reaction mixture was cooled to room temperature, water (200 mL) was added, and the mixture was extracted with ethyl acetate (2×100 mL). The combined extracts were washed with water (100 mL), dried (magnesium sulfate), filtered, and evaporated to solid (0.97 g). This residue was purified by chromatography (silica gel, ethyl acetate gradient) and recrystallized from methanol and ethyl acetate to give a colorless solid (0.18 g, 18%): mp 162–164° C.; LC/MS m/z 286.

Workup

  1. additionwas added
  2. customthe mixture was evaporated to a residue which
  3. dissolutiondissolved in dimethyl sulfoxide (20 mL)
  4. temperatureThe reaction mixture was cooled to room temperature
  5. additionwater (200 mL) was added
  6. extractionthe mixture was extracted with ethyl acetate (2×100 mL)
  7. washThe combined extracts were washed with water (100 mL)
  8. dry with materialdried (magnesium sulfate)
  9. filtrationfiltered
  10. customevaporated to solid (0.97 g)
  11. customThis residue was purified by chromatography (silica gel, ethyl acetate gradient)
  12. customrecrystallized from methanol and ethyl acetate

Sources & evidence

ORD record
ord-98ee36de372740f4a74afb5bf7424b81
Source dataset
uspto-grants-2006_10
Patent number
US07129257B1

Reaction notes

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