Sodium Hydroxide → HCID 70647861, compound

HRID 2202583Notes

Reaction equation

HRID 2202583 reaction equation
[CH:1]([O:14][CH:15]1[CH2:20][CH2:19][N:18]([C:21]([F:33])([F:32])[C:22]2[N:27]=[C:26]([C:28]([O:30]C)=[O:29])[CH:25]=[CH:24][CH:23]=2)[CH2:17][CH2:16]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C>[CH:1]([O:14][CH:15]1[CH2:16][CH2:17][N:18]([C:21]([F:33])([F:32])[C:22]2[N:27]=[C:26]([C:28]([OH:30])=[O:29])[CH:25]=[CH:24][CH:23]=2)[CH2:19][CH2:20]1)([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 70647870HCID 70647870, compound

Product 1

HCID 70647861HCID 70647861, compoundYield 83.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Into a 50-mL recovery flask (eggplant flask), 380 mg (0.84 mmol) of methyl 6-[(4-benzhydryloxypiperidin-1-yl)difluoromethyl]pyridine-2-carboxylate synthesized in Production Example 51 was fed and dissolved in 10 mL of ethanol. Thereto, 1.7 mL of a 1-N sodium hydroxide aqueous solution was added, and the reaction was conducted at a room temperature. After the completion of the reaction was confirmed, the contents in the system were concentrated, and the residue was diluted with water. The diluted residue was neutralized with 1-N hydrochloric acid and then extracted with chloroform. The organic layer was washed with water and a saturated saline solution in order and then dried over sodium sulfate. After the solvent was concentrated, the resulting brown oily substance was purified by column chromatography (chloroform/methanol (volume ratio)=3:1) to give the title compound (306 mg (83%)).

Workup

  1. customwas conducted at a room temperature
  2. concentrationthe contents in the system were concentrated
  3. additionthe residue was diluted with water
  4. extractionextracted with chloroform
  5. washThe organic layer was washed with water
  6. dry with materiala saturated saline solution in order and then dried over sodium sulfate
  7. concentrationAfter the solvent was concentrated
  8. customthe resulting brown oily substance was purified by column chromatography (chloroform/methanol (volume ratio)=3:1)

Sources & evidence

ORD record
ord-ba59d0bcfe2d456e92e1067074108d9a
Source dataset
uspto-grants-2016_06
Patent number
US09365553B2

Reaction notes

Loading…