Hydrochloric Acid → 1-Benzyl-8-hydroxy-2-oxo-1,2-dihydro-[1,6]naphthyridine-7-carboxylic acid methyl ester

HRID 919784Notes

Reaction equation

HRID 919784 reaction equation
C([O:3][C:4]([C:6]1[N:7]([CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:8](=[O:29])[CH:9]=[CH:10][C:11]=1[CH2:12][N:13]([CH2:24][C:25]([O:27][CH3:28])=[O:26])S(C1C=CC(C)=CC=1)(=O)=O)=O)C.C[O-].[Na+].Cl>CO>[CH3:28][O:27][C:25]([C:24]1[C:4]([OH:3])=[C:6]2[C:11]([CH:10]=[CH:9][C:8](=[O:29])[N:7]2[CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[CH:12][N:13]=1)=[O:26]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 682976731-Benzyl-3-{[methoxycarbonylmethyl-(toluene-4-sulfonyl)-amino]-methyl}-6-oxo-1,6-dihydro-pyridine-2-carboxylic acid ethyl ester

Product 1

HCID 682971941-Benzyl-8-hydroxy-2-oxo-1,2-dihydro-[1,6]naphthyridine-7-carboxylic acid methyl esterYield 90.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-Benzyl-3-{[methoxycarbonylmethyl-(toluene-4-sulfonyl)-amino]-methyl}-6-oxo-1,6-dihydro-pyridine-2-carboxylic acid ethyl ester (0.14 g, 0.27 mmol) was dissolved in MeOH (10 mL) and cooled in an ice bath. NaOMe solution (0.2 mL, 0.82 mmol, 25 wt % in MeOH) was added, and the mixture was stirred overnight. The mixture was placed in an ice bath, and 1 M HCl was added until pH was about 3. The resulting mixture was extracted with CH2Cl2. The organic layer was dried over MgSO4 and concentrated. The residue was chromatographed (10-90% EtOAc/hexanes+2% AcOH) to give 76 mg of the title compound. MS: (−) m/z 311.30 (M+1).

Workup

  1. temperaturecooled in an ice bath
  2. customThe mixture was placed in an ice bath
  3. extractionThe resulting mixture was extracted with CH2Cl2
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was chromatographed (10-90% EtOAc/hexanes+2% AcOH)

Sources & evidence

ORD record
ord-1c628aebd6f3493e8cb405d224a6b6e4
Source dataset
uspto-grants-2016_03
Patent number
US09271970B2

Reaction notes

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