Reaction equation
[N:1]1[C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=[CH:3][C:2]=1C(O)=O.C([N:15]([CH2:18]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:27])C=CC=CC=1.[C:37]([OH:41])([CH3:40])([CH3:39])[CH3:38]>>[C:37]([O:41][C:18]([NH:15][C:2]1[N:1]=[C:6]([C:7]([OH:9])=[O:8])[CH:5]=[CH:4][CH:3]=1)=[O:27])([CH3:40])([CH3:39])[CH3:38]Participants
Procedure
To a suspension of 2,6-pyridinedicarboxylic acid (8.35 g, 50 mmol) and triethylamine (5.05 g, 50 mmol) in tert-butyl alcohol (ca. 60 mL) was dropwise added diphenylphosphoryl azide (13.8 g, 50 mmol), and the mixture was stirred at room temperature until the reaction mixture became a clear solution. The solution was then slowly heated and refluxed for 2.5 hour. After cooling, the mixture was partitioned between ethyl acetate/hexane (1:1, v/v) and 1% aqueous sodium hydroxide. The organic layer was washed again with 1% aqueous sodium hydroxide. All the aqueous solutions were combined and neutralized to pH=5 with concentrated hydrochloric acid in the presence of ethyl acetate. The ethyl acetate layer was washed with brine, dried over sodium sulfate and concentrated to obtain 5.0 g of 6-tert-butoxycarbonylamino-2-pyridinecarboxylic acid.
Workup
- temperatureThe solution was then slowly heated
- temperaturerefluxed for 2.5 hour
- temperatureAfter cooling
- customthe mixture was partitioned between ethyl acetate/hexane (1:1
- washThe organic layer was washed again with 1% aqueous sodium hydroxide
- washThe ethyl acetate layer was washed with brine
- dry with materialdried over sodium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-90433118cead4a0b91bd2ff96b3947a0
- Source dataset
- uspto-grants-2000_02
- Patent number
- US06030965
Linked notes
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