Hydrochloric Acid → 6-tert-butoxycarbonyl-2-methoxy-7,8-dihydro-5H-1,6-naphthyridine-5-carboxylic acid
Reaction equation
[OH-].[Li+].[CH3:3][O:4][C:5]1[CH:14]=[CH:13][C:12]2[CH:11]([C:15]([O:17]CC)=[O:16])[N:10]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:9][CH2:8][C:7]=2[N:6]=1.CCO.Cl>O.C1COCC1>[C:23]([O:22][C:20]([N:10]1[CH2:9][CH2:8][C:7]2[N:6]=[C:5]([O:4][CH3:3])[CH:14]=[CH:13][C:12]=2[CH:11]1[C:15]([OH:17])=[O:16])=[O:21])([CH3:26])([CH3:24])[CH3:25]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
2N Aqueous lithium hydroxide solution (61.8 mL, 123.61 mmol) was added to a solution of 5-ethyl 6-tert-butyl 2-methoxy-7,8-dihydro-1,6-naphthyridine-5,6(5H)-dicarboxylate (6.93 g, 20.60 mmol) in a mixed solvent of EtOH (30 mL) and THF (30 mL) at room temperature, and the mixture was stirred at room temperature for 1.5 hr. The reaction mixture was poured into ice-cooled water, and the pH of the mixture was adjusted to 4 with 6N hydrochloric acid. Then, the mixture was extracted with a mixed solvent of mixed ethyl acetate/THF (3:1) (×3). The organic layer was washed with water and brine, and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure to give 6-(tert-butoxycarbonyl)-2-methoxy-5,6,7,8-tetrahydro-1,6-naphthyridine-5-carboxylic acid (6.37 g, 20.66 mmol, 100%) as a colorless amorphous solid.
Workup
- additionThe reaction mixture was poured into ice-
- extractionThen, the mixture was extracted with a mixed solvent of mixed ethyl acetate/THF (3:1) (×3)
- washThe organic layer was washed with water and brine
- dry with materialdried over magnesium sulfate
- customthe solvent was evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-16d266111fef4f28b983abbe69929be2
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09365520B2
Reaction notes
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