Triethylamine → HCID 131724353, compound

HRID 2121904Notes

Reaction equation

HRID 2121904 reaction equation
O[C@H:2]([CH3:24])[CH2:3][N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]3[O:16][CH2:15][C@H:14]([O:17][CH2:18][CH2:19][NH:20][C:21](=[O:23])[CH3:22])[CH2:13][C:11]3=2)[CH:6]=[N:5]1.C(N(CC)CC)C.CS(OS(C)(=O)=O)(=O)=O.[N-:41]=[N+:42]=[N-:43].[Na+]>C1COCC1>[N:41]([C@@H:2]([CH3:24])[CH2:3][N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]3[O:16][CH2:15][C@H:14]([O:17][CH2:18][CH2:19][NH:20][C:21](=[O:23])[CH3:22])[CH2:13][C:11]3=2)[CH:6]=[N:5]1)=[N+:42]=[N-:43]

Participants

6

Reactant 4

HCID 8471Triethylamine2×HCID 33557Sodium AzideHCID 81560Methanesulfonic anhydride2×HCID 69709561HCID 69709561, compound

Product 1

HCID 131724353HCID 131724353, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
90 °C

Procedure

To a cooled (0° C.) solution of the product from Step D (0.23 g, 0.69 mmol) and triethylamine (0.28 g, 0.38 mL, 2.76 mmol, 4.0 equiv.) in anhydrous THF (50 mL) was added methanesulfonic anhydride (0.19 g, 1.1 mmol, 1.6 equiv.). The mixture was stirred for 30 min, additional triethylamine and methanesulfonic anhydride (1.6 equiv.) were added and stirred for 1 h. Sodium azide (0.45 g, 6.9 mmol, 10 equiv.) was added and the solvent was evaporated to a residue. Anhydrous dimethyl sulfoxide (20 mL) was added and the mixture heated at 90° C. for 3 h. The mixture was cooled, poured into a saturated solution of sodium bicarbonate (60 mL) and extracted with ethyl acetate (3×50 mL). The combined extracts were dried (MgSO4) and evaporated to a residue which was purified by chromatography (silica, ethyl acetate) to give an oil (0.20 g, 81%).

Workup

  1. stirringstirred for 1 h
  2. customthe solvent was evaporated to a residue
  3. additionAnhydrous dimethyl sulfoxide (20 mL) was added
  4. temperatureThe mixture was cooled
  5. additionpoured into a saturated solution of sodium bicarbonate (60 mL)
  6. extractionextracted with ethyl acetate (3×50 mL)
  7. dry with materialThe combined extracts were dried (MgSO4)
  8. customevaporated to a residue which
  9. customwas purified by chromatography (silica, ethyl acetate)

Sources & evidence

ORD record
ord-239d00e2da254aa7a902303f69412cfc
Source dataset
uspto-grants-2004_02
Patent number
US06696476B2

Reaction notes

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