Hydrochloric Acid → 3-[(1-Benzyl-8-cyano-5-hydroxy-2-oxo-3-phenyl-1,2-dihydro-[1,7]naphthyridine-6-carbonyl)-amino]-2,2-dimethyl-propionic acid

HRID 1410711Notes

Reaction equation

HRID 1410711 reaction equation
C[O:2][C:3](=[O:38])[C:4]([CH3:37])([CH3:36])[CH2:5][NH:6][C:7]([C:9]1[C:10]([OH:35])=[C:11]2[C:16](=[C:17]([C:19]#[N:20])[N:18]=1)[N:15]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:14](=[O:28])[C:13]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[CH:12]2)=[O:8].[OH-].[Na+].Cl>CO>[CH2:21]([N:15]1[C:16]2[C:11](=[C:10]([OH:35])[C:9]([C:7]([NH:6][CH2:5][C:4]([CH3:37])([CH3:36])[C:3]([OH:38])=[O:2])=[O:8])=[N:18][C:17]=2[C:19]#[N:20])[CH:12]=[C:13]([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:14]1=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 682974863-[(1-Benzyl-8-cyano-5-hydroxy-2-oxo-3-phenyl-1,2-dihydro-[1,7]naphthyridine-6-carbonyl)-amino]-2,2-dimethyl-propionic acid methyl ester

Product 1

HCID 601526343-[(1-Benzyl-8-cyano-5-hydroxy-2-oxo-3-phenyl-1,2-dihydro-[1,7]naphthyridine-6-carbonyl)-amino]-2,2-dimethyl-propionic acidYield 53.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 3-[(1-benzyl-8-cyano-5-hydroxy-2-oxo-3-phenyl-1,2-dihydro-[1,7]naphthyridine-6-carbonyl)-amino]-2,2-dimethyl-propionic acid methyl ester (50 mg, 0.098 mmol), 2M NaOH (3 mL) and MeOH (3 mL) was stirred at r.t. for 1 h. 1M 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 crude product was chromatographed (0-30% EtOAc/hexanes+2% AcOH) to give 26 mg of the title compound. MS: (+) m/z 497.15 (M+1).

Workup

  1. extractionthe resulting suspension was extracted with EtOAc
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated
  4. customThe crude product was chromatographed (0-30% EtOAc/hexanes+2% AcOH)

Sources & evidence

ORD record
ord-3425e8a176d54c58bc7302ae8549911c
Source dataset
uspto-grants-2014_12
Patent number
US08921389B2

Reaction notes

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