Sodium Hydroxide → HCID 118037906, compound

HRID 2272516Notes

Reaction equation

HRID 2272516 reaction equation
[OH-].[Na+].[CH:3]1([C:6]2[C:11]([C:12]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=3[F:19])=[C:10]([F:20])[C:9]([O:21][CH2:22][CH3:23])=[C:8]([CH2:24][N:25]3[CH2:30][CH2:29][CH:28]([N:31]4[CH:36]=[CH:35][C:34]([C:37]([O:39]C)=[O:38])=[C:33]([CH2:41][CH3:42])[C:32]4=[O:43])[CH2:27][CH2:26]3)[CH:7]=2)[CH2:5][CH2:4]1>C(O)C>[CH:3]1([C:6]2[C:11]([C:12]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=3[F:19])=[C:10]([F:20])[C:9]([O:21][CH2:22][CH3:23])=[C:8]([CH2:24][N:25]3[CH2:26][CH2:27][CH:28]([N:31]4[CH:36]=[CH:35][C:34]([C:37]([OH:39])=[O:38])=[C:33]([CH2:41][CH3:42])[C:32]4=[O:43])[CH2:29][CH2:30]3)[CH:7]=2)[CH2:5][CH2:4]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 118037639HCID 118037639, compound

Product 1

HCID 118037906HCID 118037906, compoundYield 67.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 2 M aqueous sodium hydroxide solution (1.5 mL) was added to an ethanol (6 mL) solution of methyl 1-(1-((6-cyclopropyl-3-ethoxy-2,2′,4′-trifluorobiphenyl-4-yl)methyl)piperidin-4-yl)-3-ethyl-2-oxo-1,2-dihydropyridine-4-carboxylate (264 mg), and the mixture was stirred at 80 C for 3 hours in a nitrogen atmosphere. Then, the solvent was distilled off under reduced pressure. Water was added to the residue, and the mixture was neutralized with 2 M hydrochloric acid, followed by extraction with a mixed solution of ethyl acetate and THF. The organic layer was separated, then washed with water and saturated saline in this order, and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was crystallized (hexane/ethyl acetate) and further recrystallized (hexane/ethanol) to obtain the title compound (173 mg).

Workup

  1. distillationThen, the solvent was distilled off under reduced pressure
  2. additionWater was added to the residue
  3. extractionfollowed by extraction with a mixed solution of ethyl acetate and THF
  4. customThe organic layer was separated
  5. washwashed with water and saturated saline in this order
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe obtained residue was crystallized (hexane/ethyl acetate)
  9. customfurther recrystallized (hexane/ethanol)

Sources & evidence

ORD record
ord-eeaedcf938f44b4ca418e9f6c91e3500
Source dataset
uspto-grants-2015_09
Patent number
US09120777B2

Reaction notes

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