Methanol → HCID 68297228, compound

HRID 1411020Notes

Reaction equation

HRID 1411020 reaction equation
C([O:3][C:4]([C:6]1([NH:9][C:10]([C:12]2[C:13]([OH:36])=[C:14]3[C:19](=[CH:20][N:21]=2)[N:18]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17](=[O:29])[C:16]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[CH:15]3)=[O:11])[CH2:8][CH2:7]1)=[O:5])C.[OH-].[Na+].CO.C1COCC1>C([O-])(O)=O.[Na+]>[CH2:22]([N:18]1[C:19]2[C:14](=[C:13]([OH:36])[C:12]([C:10]([NH:9][C:6]3([C:4]([OH:5])=[O:3])[CH2:8][CH2:7]3)=[O:11])=[N:21][CH:20]=2)[CH:15]=[C:16]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:17]1=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 68297375HCID 68297375, compound

Product 1

HCID 68297228HCID 68297228, compoundYield 39.7%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

A mixture of 1-[(1-benzyl-5-hydroxy-2-oxo-3-phenyl-1,2-dihydro-[1,7]naphthyridine-6-carbonyl)-amino]-cyclopropanecarboxylic acid ethyl ester (40 mg, 0.083 mmol), 2 M NaOH (3 mL), MeOH (3 mL) and THF (3 mL) was stirred at r.t. for 16 h, then concentrated to approximately one-third of its original volume. 1 M HCl was added to acidify the mixture, and the resulting suspension was extracted with EtOAc. The organic layer was dried over MgSO4 and concentrated. The residue was dissolved in saturated NaHCO3 and washes several times with ether. The aqueous layer was acidified to pH about 3, and the resulting precipitate was isolated by filtration. The crude solid was purified by silica gel chromatography (5-60% EtOAc/hexanes+1% AcOH). The product isolated was dissolved in saturated NaHCO3 and washed several times with ether. The aqueous layer was acidified to pH about 3, and the resulting precipitate was isolated by filtration to give 15 mg of the title compound. MS: (+) m/z 456.35 (M+1).

Workup

  1. concentrationconcentrated to approximately one-third of its original volume
  2. addition1 M HCl was added
  3. extractionthe resulting suspension was extracted with EtOAc
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated
  6. dissolutionThe residue was dissolved in saturated NaHCO3
  7. customthe resulting precipitate was isolated by filtration
  8. customThe crude solid was purified by silica gel chromatography (5-60% EtOAc/hexanes+1% AcOH)
  9. customThe product isolated
  10. washwashed several times with ether
  11. customthe resulting precipitate was isolated by filtration

Sources & evidence

ORD record
ord-f07a3407a626480e9302ad68259dd1fc
Source dataset
uspto-grants-2014_12
Patent number
US08921389B2

Reaction notes

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