Sodium Hydroxide → HCID 118037955, compound

HRID 2272523Notes

Reaction equation

HRID 2272523 reaction equation
[OH-].[Na+].[CH:3]1([C:6]2[C:31]([CH:32]3[CH2:34][CH2:33]3)=[CH:30][C:9]([CH2:10][N:11]3[CH2:16][CH2:15][CH:14]([N:17]4[CH:22]=[CH:21][C:20]([C:23]([O:25]C)=[O:24])=[C:19]([CH2:27][CH3:28])[C:18]4=[O:29])[CH2:13][CH2:12]3)=[C:8]([O:35][CH:36]([CH3:38])[CH3:37])[C:7]=2[F:39])[CH2:5][CH2:4]1>C(O)C>[CH:3]1([C:6]2[C:31]([CH:32]3[CH2:33][CH2:34]3)=[CH:30][C:9]([CH2:10][N:11]3[CH2:12][CH2:13][CH:14]([N:17]4[CH:22]=[CH:21][C:20]([C:23]([OH:25])=[O:24])=[C:19]([CH2:27][CH3:28])[C:18]4=[O:29])[CH2:15][CH2:16]3)=[C:8]([O:35][CH:36]([CH3:38])[CH3:37])[C:7]=2[F:39])[CH2:5][CH2:4]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 118037569HCID 118037569, compound

Product 1

HCID 118037955HCID 118037955, compoundYield 74.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 2 M aqueous sodium hydroxide solution (2 mL) was added to an ethanol (8 mL) solution of methyl 1-(1-(4,5-dicyclopropyl-3-fluoro-2-isopropoxybenzyl)piperidin-4-yl)-3-ethyl-2-oxo-1,2-dihydropyridine-4-carboxylate (358 mg), and the mixture was stirred at 80 C for 3 hours in a nitrogen atmosphere. The solvent in the reaction mixture was distilled off under reduced pressure. The obtained residue was dissolved in water, and the solution was neutralized with 2 M hydrochloric acid, followed by extraction with a mixed solution of ethyl acetate and THF. The obtained organic layer was washed with water and saturated saline in this order and dried over anhydrous magnesium sulfate, and then, the solvent was distilled off under reduced pressure. The obtained residue was crystallized (ethyl acetate/hexane) and further recrystallized (ethyl acetate/hexane) to obtain the title compound (258 mg).

Workup

  1. distillationThe solvent in the reaction mixture was distilled off under reduced pressure
  2. dissolutionThe obtained residue was dissolved in water
  3. extractionfollowed by extraction with a mixed solution of ethyl acetate and THF
  4. washThe obtained organic layer was washed with water and saturated saline in this order
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe obtained residue was crystallized (ethyl acetate/hexane)
  8. customfurther recrystallized (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-2830bb8ea7154cfab3d3017286e944c9
Source dataset
uspto-grants-2015_09
Patent number
US09120777B2

Reaction notes

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