Methanol → HCID 135981263, compound

HRID 1411030Notes

Reaction equation

HRID 1411030 reaction equation
C[O:2][C:3](=[O:40])[CH2:4][CH2:5][NH:6][C:7]([C:9]1[C:10]([OH:39])=[C:11]2[C:16](=[C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=3)[N:18]=1)[N:15]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:14](=[O:32])[C:13]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[CH:12]2)=[O:8].[OH-].[Na+].CO.C1COCC1>C([O-])(O)=O.[Na+]>[CH2:25]([N:15]1[C:16]2[C:11](=[C:10]([OH:39])[C:9]([C:7]([NH:6][CH2:5][CH2:4][C:3]([OH:40])=[O:2])=[O:8])=[N:18][C:17]=2[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)[CH:12]=[C:13]([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[C:14]1=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 136377246HCID 136377246, compound

Product 1

HCID 135981263HCID 135981263, compoundYield 29.8%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

A mixture of 3-[(1-benzyl-5-hydroxy-2-oxo-3-phenyl-8-pyridin-2-yl-1,2-dihydro-[1,7]naphthyridine-6-carbonyl)-amino]-propionic acid methyl ester (62 mg, 0.116 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 until pH was about 3-4, and the resulting suspension was extracted with EtOAc. The organic layer was dried over MgSO4 and concentrated. The crude product was purified twice by silica gel chromatography (100% EtOAc, then 10-60% 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 3-4, and the resulting precipitate was isolated by filtration to give 18 mg of the title compound. MS: (+) m/z 521.41 (M+1).

Workup

  1. concentrationconcentrated to approximately one-third of its original volume
  2. addition1 M HCl was added until pH was about 3-4
  3. extractionthe resulting suspension was extracted with EtOAc
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated
  6. customThe crude product was purified twice by silica gel chromatography (100% EtOAc
  7. customThe product isolated
  8. washwashed several times with ether
  9. customthe resulting precipitate was isolated by filtration

Sources & evidence

ORD record
ord-f4289a3b0d28495f800c582065ebd011
Source dataset
uspto-grants-2014_12
Patent number
US08921389B2

Reaction notes

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