Hydrochloric Acid → 1-Benzyl-5-hydroxy-2-oxo-1,2-dihydro-[1,7]naphthyridine-6-carboxylic acid methyl ester

HRID 1410676Notes

Reaction equation

HRID 1410676 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8](=[O:11])[N:7]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:6]=1[CH2:19][N:20]([CH2:31][C:32]([O:34][CH3:35])=[O:33])S(C1C=CC(C)=CC=1)(=O)=O)=O.C[O-].[Na+].[NH4+].[Cl-].Cl>CO>[CH3:35][O:34][C:32]([C:31]1[C:3]([OH:2])=[C:5]2[C:6](=[CH:19][N:20]=1)[N:7]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:8](=[O:11])[CH:9]=[CH:10]2)=[O:33]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 10942334Sodium MethoxideHCID 682976291-Benzyl-2-{[methoxycarbonylmethyl-(toluene-4-sulfonyl)-amino]-methyl}-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid methyl ester

Product 1

HCID 682974351-Benzyl-5-hydroxy-2-oxo-1,2-dihydro-[1,7]naphthyridine-6-carboxylic acid methyl esterYield 83.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-Benzyl-2-{[methoxycarbonylmethyl-(toluene-4-sulfonyl)-amino]-methyl}-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid methyl ester (2 g, 4.02 mmol) was dissolved in 60 mL of MeOH. NaOMe solution (3 mL, 12.5 mmol, 25 wt % in MeOH) was added and the mixture was stirred for 16 h. Saturated NH4Cl (100 mL) was added, followed by addition of 1M HCl until pH about 2. The resulting mixture was extracted several times with CH2Cl2. The organic layers were combined, dried over MgSO4, and concentrated in vacuo. The crude product was purified by silica gel chromatography (0-60% EtOAc/hexanes+2% AcOH) to give 1.04 g of the title compound as a white solid. MS: (+) m/z 311.05 (M+1).

Workup

  1. extractionThe resulting mixture was extracted several times with CH2Cl2
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified by silica gel chromatography (0-60% EtOAc/hexanes+2% AcOH)

Sources & evidence

ORD record
ord-26e5d3f452574ccfa87137633079b53e
Source dataset
uspto-grants-2014_12
Patent number
US08921389B2

Reaction notes

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