Glycine → [(6-Benzyl-4-hydroxy-5-oxo-5,6-dihydro-[2,6]naphthyridine-3-carbonyl)-amino]-acetic acid
Reaction equation
CO[C:3]([C:5]1[N:6]=[CH:7][C:8]2[CH:9]=[CH:10][N:11]([CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:12](=[O:16])[C:13]=2[C:14]=1[OH:15])=[O:4].[NH2:24][CH2:25][C:26]([OH:28])=[O:27].C[O-].[Na+]>>[CH2:17]([N:11]1[CH:10]=[CH:9][C:8]2[CH:7]=[N:6][C:5]([C:3]([NH:24][CH2:25][C:26]([OH:28])=[O:27])=[O:4])=[C:14]([OH:15])[C:13]=2[C:12]1=[O:16])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1Participants
4
Procedure
A mixture of 6-benzyl-4-hydroxy-5-oxo-5,6-dihydro-[2,6]naphthyridine-3-carboxylic acid methyl ester (25 mg, 0.081 mmol), glycine (805 mg, 10.7 mmol) and NaOMe solution (16 mL, 8.06 mmol, 0.5 M in MeOH) was refluxed for 16 h. Solvent was evaporated in vacuo, and the residue was partitioned between water and EtOAc. 1 M HCl was added with vigorous stirring until pH was about 2. The organic layer was dried over MgSO4 and concentrated. The crude solid was dissolved in saturated NaHCO3 and washed with ether. The aqueous layer was acidified to pH about 2 with 4 M HCl, and then extracted with EtOAc. The organic layer was dried over MgSO4 and concentrated to give 20 mg of the title compound as a yellow solid. MS: (+)
Workup
- temperaturewas refluxed for 16 h
- customSolvent was evaporated in vacuo
- customthe residue was partitioned between water and EtOAc
- addition1 M HCl was added
- dry with materialThe organic layer was dried over MgSO4
- concentrationconcentrated
- dissolutionThe crude solid was dissolved in saturated NaHCO3
- washwashed with ether
- extractionextracted with EtOAc
- dry with materialThe organic layer was dried over MgSO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-71ae1099faa8475783fa9cce5dfe84a2
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09271970B2
Reaction notes
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