Triethylamine → HCID 86759656, compound
Reaction equation
[N:1]1([CH2:14][C@H:15](O)[CH3:16])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]3[O:13][CH2:12][CH:11]=[CH:10][C:8]3=2)[CH:3]=[N:2]1.C(N(CC)CC)C.CS(OS(C)(=O)=O)(=O)=O.[N-:34]=[N+:35]=[N-:36].[Na+]>C1COCC1>[N:34]([C@@H:15]([CH3:16])[CH2:14][N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]3[O:13][CH2:12][CH:11]=[CH:10][C:8]3=2)[CH:3]=[N:2]1)=[N+:35]=[N-:36]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 110 °C
Procedure
To a solution of the product from Step A (0.14 g, 0.61 mmol) and triethylamine (0.18 g, 1.8 mmol) in anhydrous THF (50 ml) at 0° C. was added methanesulfonic anhydride (0.16 g, 0.92 mmol). The mixture was stirred for 10 min and sodium azide (0.40 g, 6.1 mmol) was added; the solvent was evaporated and anhydrous DMF (50 mL) added followed by heating at 110° C. for 3 h. The mixture was cooled, poured into a saturated solution of sodium bicarbonate (80 mL) and extracted with ethyl acetate (3×60 mL). The combined extracts were dried, filtered, and evaporated to a residue which was purified by chromatography (silica, 10% ethyl acetate in hexane) to give an oil (0.06 g, 39%): LC/MS (+APCI) m/z 256 (M+H).
Workup
- customthe solvent was evaporated
- additionanhydrous DMF (50 mL) added
- temperatureThe mixture was cooled
- additionpoured into a saturated solution of sodium bicarbonate (80 mL)
- extractionextracted with ethyl acetate (3×60 mL)
- customThe combined extracts were dried
- filtrationfiltered
- customevaporated to a residue which
- customwas purified by chromatography (silica, 10% ethyl acetate in hexane)
Sources & evidence
- ORD record
- ord-5408b9f65ed2412a95cf48822e0e94f2
- Source dataset
- uspto-grants-2005_04
- Patent number
- US06881749B2
Reaction notes
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