Triethylamine → HCID 86662093, compound
Reaction equation
[F:1][C:2]1[C:7]([C:8](=[O:15])[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:6][CH:5]=[CH:4][N:3]=1.C(N(CC)CC)C.C(NC1C=CC(S([N:36]=[N+:37]=[N-])(=O)=O)=CC=1)(=O)C.[OH-].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C.O>[N+:36](=[C:9]([C:8]([C:7]1[C:2]([F:1])=[N:3][CH:4]=[CH:5][CH:6]=1)=[O:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[N-:37]Participants
Conditions
- Temperature
- 0 °C
Procedure
Ethyl 3-(2-fluoropyridine-3-yl)-3-oxopropanoate (1.42 g, 6.71 mmol) was dissolved in anhydrous acetonitrile (20 mL), treated with triethylamine (0.781 mL, 1.15 equiv) and cooled to 0° C. To the mixture was added the 4-acetamidobenzenesulfonyl azide (1.77 g, 1.1 equiv) and after stirring 0° C. for 1 hour, the mixture was treated with sodium hydroxide (10 mL, 1 N aqueous). The mixture was poured into sodium carbonate (50 mL, aqueous saturated) and water (200 mL) and extracted with ethyl acetate (2×250 mL). The combined organic extracts were washed once with brine (50 mL), dried with sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel gradient chromatography (100:0 to 70:30; hexanes:ethyl acetate), providing the titled compound as a light yellow oil.
Workup
- extractionextracted with ethyl acetate (2×250 mL)
- washThe combined organic extracts were washed once with brine (50 mL)
- dry with materialdried with sodium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe residue was purified by silica gel gradient chromatography (100:0 to 70:30; hexanes:ethyl acetate)
Sources & evidence
- ORD record
- ord-8dc45150fd9447d8b277c7ad3f186c5e
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08293744B2
Reaction notes
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