Sodium Hydroxide → HCID 118038010, compound

HRID 2272478Notes

Reaction equation

HRID 2272478 reaction equation
[OH-].[Na+].[CH:3]1([C:6]2[C:29]([CH:30]3[CH2:32][CH2:31]3)=[CH:28][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])=[CH:19][C:18]4=[O:27])[CH2:13][CH2:12]3)=[C:8]([O:33][CH:34]([CH3:36])[CH3:35])[CH:7]=2)[CH2:5][CH2:4]1>C(O)C>[CH:3]1([C:6]2[C:29]([CH:30]3[CH2:31][CH2:32]3)=[CH:28][C:9]([CH2:10][N:11]3[CH2:16][CH2:15][CH:14]([N:17]4[CH:22]=[CH:21][C:20]([C:23]([OH:25])=[O:24])=[CH:19][C:18]4=[O:27])[CH2:13][CH2:12]3)=[C:8]([O:33][CH:34]([CH3:36])[CH3:35])[CH:7]=2)[CH2:4][CH2:5]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 118037554HCID 118037554, compound

Product 1

HCID 118038010HCID 118038010, compoundYield 69.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 2 M aqueous sodium hydroxide solution (3 mL) was added to an ethanol (8 mL) solution of methyl 1-(1-(4,5-dicyclopropyl-2-isopropoxybenzyl)piperidin-4-yl)-2-oxo-1,2-dihydropyridine-4-carboxylate (426 mg), and the mixture was stirred at 90 C for 2 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. The resulting solid was collected by filtration and dissolved in ethyl acetate and THF. The solvent in the obtained solution was distilled off under reduced pressure. The obtained residue was crystallized (ethyl acetate/hexane) and recrystallized (ethanol/hexane) to obtain the title compound (286 mg).

Workup

  1. distillationThe solvent in the reaction mixture was distilled off under reduced pressure
  2. dissolutionThe obtained residue was dissolved in water
  3. filtrationThe resulting solid was collected by filtration
  4. dissolutiondissolved in ethyl acetate
  5. distillationThe solvent in the obtained solution was distilled off under reduced pressure
  6. customThe obtained residue was crystallized (ethyl acetate/hexane)
  7. customrecrystallized (ethanol/hexane)

Sources & evidence

ORD record
ord-0f4a648d10644ebc98545eb0f09f56c0
Source dataset
uspto-grants-2015_09
Patent number
US09120777B2

Reaction notes

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