Lithium Hydroxide → HCID 69066186, compound

HRID 1817320Notes

Reaction equation

HRID 1817320 reaction equation
[F:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][N:7]2[CH2:16][CH2:15][C:14]3[C:9](=[C:10]([O:23][CH3:24])[C:11](=[O:22])[N:12]([CH3:21])[C:13]=3[C:17]([O:19]C)=[O:18])[C:8]2=[O:25])=[CH:4][CH:3]=1.[Li+].[OH-]>CO.O>[F:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][N:7]2[CH2:16][CH2:15][C:14]3[C:9](=[C:10]([O:23][CH3:24])[C:11](=[O:22])[N:12]([CH3:21])[C:13]=3[C:17]([OH:19])=[O:18])[C:8]2=[O:25])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 69065040HCID 69065040, compound

Product 1

HCID 69066186HCID 69066186, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of methyl 6-(4-fluorobenzyl)-4-methoxy-2-methyl-3,5-dioxo-2,3,5,6,7,8-hexahydro-2,6-naphthyridine-1-carboxylate (0.575 g, 1.536 mmol) in methanol was added LiOH (0.11 g, 4.61 mmol) in water. The reaction mixture was heated to reflux. After 0.5 hours, the product mixture cooled to room temperature and concentrated under vacuum. The residual material was partitioned between EtOAc and 1 N HCl. The organic extract was washed with brine, dried with Na2SO4, filtered, and concentrated under vacuum to provide the title compound.

Workup

  1. temperatureThe reaction mixture was heated to reflux
  2. concentrationconcentrated under vacuum
  3. customThe residual material was partitioned between EtOAc and 1 N HCl
  4. extractionThe organic extract
  5. washwas washed with brine
  6. dry with materialdried with Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-53395053f19f4d61aeab47732fe92dec
Source dataset
uspto-grants-2009_10
Patent number
US07598264B2

Reaction notes

Loading…