Methanol → HCID 60152242, compound

HRID 920019Notes

Reaction equation

HRID 920019 reaction equation
C([O:3][C:4](=[O:38])[CH2:5][CH2:6][CH2:7][NH:8][C:9]([C:11]1[C:12]([OH:37])=[C:13]2[C:18](=[CH:19][N:20]=1)[N:17]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16](=[O:28])[C:15]([C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([O:35][CH3:36])[CH:30]=1)=[CH:14]2)=[O:10])C.[OH-].[Na+].CO>C1COCC1>[CH2:21]([N:17]1[C:18]2[C:13](=[C:12]([OH:37])[C:11]([C:9]([NH:8][CH2:7][CH2:6][CH2:5][C:4]([OH:38])=[O:3])=[O:10])=[N:20][CH:19]=2)[CH:14]=[C:15]([C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([O:35][CH3:36])[CH:30]=2)[C:16]1=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 68297221HCID 68297221, compound

Product 1

HCID 60152242HCID 60152242, compoundYield 66.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-{[1-benzyl-5-hydroxy-3-(3-methoxy-phenyl)-2-oxo-1,2-dihydro-[1,7]naphthyridine-6-carbonyl]-amino}-butyric acid ethyl ester (38 mg, 0.074 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 to give 24 mg of the title compound as a yellow solid. MS: (+) m/z 488.40 (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

Sources & evidence

ORD record
ord-77d5a69cf31b4acb84f3a88a8d686425
Source dataset
uspto-grants-2016_03
Patent number
US09271970B2

Reaction notes

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