Triethylamine → HCID 131724352, compound

HRID 2121898Notes

Reaction equation

HRID 2121898 reaction equation
[C:1]([O:5][C:6](=[O:26])[CH2:7][O:8][C@H:9]1[CH2:25][O:24][C:12]2=[CH:13][CH:14]=[C:15]3[C:19]([N:18]([CH2:20][C@H:21](O)[CH3:22])[N:17]=[CH:16]3)=[C:11]2[CH2:10]1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.CS(OS(C)(=O)=O)(=O)=O.[N-:43]=[N+:44]=[N-:45].[Na+]>C1COCC1>[C:1]([O:5][C:6](=[O:26])[CH2:7][O:8][C@H:9]1[CH2:25][O:24][C:12]2=[CH:13][CH:14]=[C:15]3[C:19]([N:18]([CH2:20][C@@H:21]([N:43]=[N+:44]=[N-:45])[CH3:22])[N:17]=[CH:16]3)=[C:11]2[CH2:10]1)([CH3:2])([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 33557Sodium AzideHCID 81560Methanesulfonic anhydrideHCID 69709981HCID 69709981, compound

Product 1

HCID 131724352HCID 131724352, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
95 °C

Procedure

To a solution of the product from Step B (0.68 g, 1.88 mmol) and triethylamine (0.76 g, 1.04 mL, 7.51 mmol, 4.0 equiv.) in anhydrous THF (50 ml) at 0° C. was added methanesulfonic anhydride (0.59 g, 3.38 mmol, 1.8 equiv.). The mixture was stirred for 10 min and sodium azide (1.22 g, 18.8 mmol, 10 equiv.) was added. The solvent was removed by evaporation and anhydrous dimethyl sulfoxide (20 mL) was added. This mixture was heated at 95° C. for 3 h, cooled, poured into a saturated solution of sodium bicarbonate (80 mL), and extracted with ethyl acetate (3×60 mL). The combined extracts were dried (MgSO4), filtered, and evaporated to an oil, which was purified by chromatography (silica, 10% ethyl acetate in hexane) to give a solid (0.61 g, 84%): mp 77-78° C.; LC/MS (+ESI) m/z 388 (M+H).

Workup

  1. customThe solvent was removed by evaporation and anhydrous dimethyl sulfoxide (20 mL)
  2. additionwas added
  3. temperaturecooled
  4. additionpoured into a saturated solution of sodium bicarbonate (80 mL)
  5. extractionextracted with ethyl acetate (3×60 mL)
  6. dry with materialThe combined extracts were dried (MgSO4)
  7. filtrationfiltered
  8. customevaporated to an oil, which
  9. customwas purified by chromatography (silica, 10% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-2b91264524a54bdaa539472ccc9dbbbc
Source dataset
uspto-grants-2004_02
Patent number
US06696476B2

Reaction notes

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