Hydrochloric Acid → HCID 178499134, compound
Reaction equation
C([O:4][C:5]1[N:6]=[C:7]([C:29]([O:31][CH2:32]C)=[O:30])[C:8]2[CH2:9][CH2:10][N:11]([CH2:20][C:21]3[CH:26]=[CH:25][C:24]([F:27])=[C:23]([Cl:28])[CH:22]=3)[C:12](=[O:19])[C:13]=2[C:14]=1[O:15]C(=O)C)(=O)C.C[O-].[Na+].Cl>CO.O1CCCC1>[Cl:28][C:23]1[CH:22]=[C:21]([CH:26]=[CH:25][C:24]=1[F:27])[CH2:20][N:11]1[CH2:10][CH2:9][C:8]2[C:7]([C:29]([O:31][CH3:32])=[O:30])=[N:6][C:5]([OH:4])=[C:14]([OH:15])[C:13]=2[C:12]1=[O:19]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of ethyl 3,4-bis(acetyloxy)-6-(3-chloro-4-fluorobenzyl)-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridine-1-carboxylate (27.8 g, 58 mmol) and sodium methoxide (41.8 mL, 232 mmol; 30% by weight solution of NaOMe in MeOH) in anhydrous methanol (300 mL) was heated at 40° C. for 5 hours. The volume of the reaction mixture was reduced by a half under vacuum, diluted with anhydrous tetrahydrofuran (400 mL), and treated with an additional solution of sodium methoxide in methanol (33 mL). The reaction mixture was stirred at room temperature overnight and then warmed to 50° C. for four hours. The product mixture was acidified with dilute hydrochloric acid to pH 3 and extracted with chloroform several times. The organic extracts were combined, dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum to provide the title compound as oil.
Workup
- temperaturewarmed to 50° C. for four hours
- extractionextracted with chloroform several times
- dry with materialdried over anhydrous sodium sulfate
- filtrationfiltered
- concentrationconcentrated under vacuum
Sources & evidence
- ORD record
- ord-d46ab850c015450d983add7eb048e45b
- Source dataset
- uspto-grants-2011_06
- Patent number
- US07968564B2
Reaction notes
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