Triethylamine → HCID 91017075, compound

HRID 2121901Notes

Reaction equation

HRID 2121901 reaction equation
[C:1]([Si:5]([CH3:28])([CH3:27])[O:6][C@H:7]([CH3:26])[CH2:8][N:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]3[O:21][CH2:20][C@H:19]([O:22][CH2:23][CH2:24]O)[CH2:18][C:16]3=2)[CH:11]=[N:10]1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.CS(OS(C)(=O)=O)(=O)=O.[N-:45]=[N+:46]=[N-:47].[Na+]>C1COCC1>[N:45]([CH2:24][CH2:23][O:22][C@H:19]1[CH2:20][O:21][C:15]2=[CH:14][CH:13]=[C:12]3[C:17]([N:9]([CH2:8][C@H:7]([O:6][Si:5]([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:27])[CH3:28])[CH3:26])[N:10]=[CH:11]3)=[C:16]2[CH2:18]1)=[N+:46]=[N-:47]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 33557Sodium AzideHCID 81560Methanesulfonic anhydrideHCID 69885950HCID 69885950, compound

Product 1

HCID 91017075HCID 91017075, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
85 °C

Procedure

To a cooled (0° C.) solution of the product from Step A (1.40 g, 3.45 mmol) and triethylamine (1.39 g, 1.92 mL, 1.38 mmol, 4.0 equiv.) in anhydrous THF (50 mL) was added methanesulfonic anhydride (1.20 g, 6.90 mmol, 2.0 equiv.). The mixture was stirred for 30 min and sodium azide (2.24 g, 34.5 mmol, 10 equiv.) was added. THF was evaporated and anhydrous dimethyl sulfoxide (50 mL) was added to the residue; this mixture was heated at 85° C. for 2 h. After cooling, the mixture was poured into a saturated solution of sodium bicarbonate (100 mL) and extracted with EtOAc (3×80 mL). The combined extracts were dried (MgSO4) and evaporated to a residue which was purified by chromatography (silica, gradient, 10% to 25% ethyl acetate in hexane) to give an oil (0.73 g, 49%): LC/MS (+ESI) m/z 432 (M+H).

Workup

  1. customTHF was evaporated
  2. additionanhydrous dimethyl sulfoxide (50 mL) was added to the residue
  3. temperatureAfter cooling
  4. additionthe mixture was poured into a saturated solution of sodium bicarbonate (100 mL)
  5. extractionextracted with EtOAc (3×80 mL)
  6. dry with materialThe combined extracts were dried (MgSO4)
  7. customevaporated to a residue which
  8. customwas purified by chromatography (silica, gradient, 10% to 25% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-4ea9d22673004f40b50c8eb4ab21c888
Source dataset
uspto-grants-2004_02
Patent number
US06696476B2

Reaction notes

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