Triethylamine → HCID 86604078, compound

HRID 1247013Notes

Reaction equation

HRID 1247013 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[O:5][C:6]2[CH:12]=[CH:11][C:10]3[CH:13]=[N:14][N:15]([CH2:16][C@H:17](O)[CH3:18])[C:9]=3[C:7]=2[N:8]=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:17]([CH3:18])[CH2:16][N:15]1[C:9]2[C:7]3[N:8]=[C:4]([CH2:3][O:2][CH3:1])[O:5][C:6]=3[CH:12]=[CH:11][C:10]=2[CH:13]=[N:14]1)=[N+:37]=[N-:38]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 33557Sodium AzideHCID 81560Methanesulfonic anhydrideHCID 69587897HCID 69587897, compound

Product 1

HCID 86604078HCID 86604078, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of the product from Step B (0.20 g, 0.77 mmol in tetrahydrofuran (10 mL) was cooled (ice bath), triethylamine (0.43 mL, 3.06 mmol) and methanesulfonic anhydride (0.24 g, 1.38 mmol) were added and the mixture was stirred at 0° C. for 20 minutes. Sodium azide (0.50 g, 7.66 mmol) was added to the reaction mixture, which was evaporated to a residue that was dissolved in dimethyl sulfoxide (10 mL) and heated at 90–100° C. for 2 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 dried (magnesium sulfate), filtered, and evaporated to give a residue which was purified by chromatography (silica gel, hexane/ethyl acetate) to give a yellow oil (80 mg, 37%): LC/MS m/z 287.

Workup

  1. additionwere added
  2. customwas evaporated to a residue that
  3. dissolutionwas dissolved in dimethyl sulfoxide (10 mL)
  4. temperatureheated at 90–100° C. for 2 hours
  5. temperatureThe reaction mixture was cooled to room temperature
  6. additionwater (200 mL) was added
  7. extractionthe mixture was extracted with ethyl acetate (2×100 mL)
  8. dry with materialThe combined extracts were dried (magnesium sulfate)
  9. filtrationfiltered
  10. customevaporated
  11. customto give a residue which
  12. customwas purified by chromatography (silica gel, hexane/ethyl acetate)

Sources & evidence

ORD record
ord-dbd05487a57449679e955f75999df481
Source dataset
uspto-grants-2006_10
Patent number
US07129257B1

Reaction notes

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