Triethylamine → HCID 22290995, compound
Reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([CH3:16])=[N:8][N:9]2[CH2:12][CH:13](O)[CH3:14])=[CH:5][CH:4]=1.C(N(CC)CC)C.CS(Cl)(=O)=O.[N-:29]=[N+:30]=[N-:31].[Na+]>ClCCl.O.CCOCC>[N:29]([CH:13]([CH3:14])[CH2:12][N:9]1[C:10]2[C:6](=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH:11]=2)[C:7]([CH3:16])=[N:8]1)=[N+:30]=[N-:31]Participants
Conditions
- Temperature
- 70 °C
Procedure
To a solution of the product from Step C (0.66 g, 3.0 mmol) in dichloromethane (10 ml) at 0° C. was added triethylamine (0.55 ml, 3.9 mmol) and methanesulfonyl chloride (0.31 ml, 3.9 mmol). After stirring for 30 min, ether (50 ml) and water (50 ml) were added. The organic layer was separated and the aqueous extracted with ether (2×50 ml). The combined ether extracts were washed with brine (30 ml), dried (MgSO4), and evaporated. The residue was taken up in DMF (6 ml) and sodium azide (0.26 g, 3.9 mmol) added. This mixture was heated at 70° C. for 12 h, poured into water, and extracted with ether (3×50 ml). The combined extracts were washed with brine, dried (MgSO4), and evaporated to a residue, which was purified by chromatography (silica, hexane to 10% ethyl acetate in hexane) to give an oil (0.51 g, 69%): MS (ES) m/z 246 (M+).
Workup
- customThe organic layer was separated
- extractionthe aqueous extracted with ether (2×50 ml)
- washThe combined ether extracts were washed with brine (30 ml)
- dry with materialdried (MgSO4)
- customevaporated
- extractionextracted with ether (3×50 ml)
- washThe combined extracts were washed with brine
- dry with materialdried (MgSO4)
- customevaporated to a residue, which
- customwas purified by chromatography (silica, hexane to 10% ethyl acetate in hexane)
Sources & evidence
- ORD record
- ord-bb7e33b2730a4b4cad30eac5dda35e98
- Source dataset
- uspto-grants-2005_10
- Patent number
- US06956036B1
Reaction notes
Loading…