Sodium Hydroxide → HCID 50996796, compound

HRID 1399604Notes

Reaction equation

HRID 1399604 reaction equation
[CH2:1]([NH:5][C:6]([CH:8]1[CH2:13][CH2:12][CH2:11][N:10]([C:14]2[N:19]=[C:18]([CH3:20])[C:17]([CH:21]([CH2:26][CH2:27][CH3:28])[C:22]([O:24]C)=[O:23])=[C:16]([C:29]3[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][CH:30]=3)[N:15]=2)[CH2:9]1)=[O:7])[CH:2]([CH3:4])[CH3:3].[OH-].[Na+]>CO>[CH2:1]([NH:5][C:6]([CH:8]1[CH2:13][CH2:12][CH2:11][N:10]([C:14]2[N:19]=[C:18]([CH3:20])[C:17]([CH:21]([CH2:26][CH2:27][CH3:28])[C:22]([OH:24])=[O:23])=[C:16]([C:29]3[CH:30]=[CH:31][C:32]([CH3:35])=[CH:33][CH:34]=3)[N:15]=2)[CH2:9]1)=[O:7])[CH:2]([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 50996616HCID 50996616, compound

Product 1

HCID 50996796HCID 50996796, compoundYield 112.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of methyl 2-(2-(3-(isobutylcarbamoyl)piperidin-1-yl)-4-methyl-6-p-tolylpyrimidin-5-yl)pentanoate (0.150 g; 0.191 mmol) in methanol (4.60 mL) was added a solution sodium hydroxide 5% (4.60 mL, 5.75 mmol) and the reaction mixturestirred at room temperature for 4 days, then heated for 18 h at 50° C. The volatiles were removed under reduced pressure, the residue was dissolved in water and the aqueous solution was washed with diethylether (3 times). The pH of the aqueous solution was adjusted between 2 and 3 by addition of a solution of hydrochloric acid 6N and the formed precipitate was collected by filtration. Purification by preparative HPLC (HPLC method 4) furnished 0.10 g (11%) of the title compound as a white solid.

Workup

  1. customthe reaction mixturestirred at room temperature for 4 days
  2. customThe volatiles were removed under reduced pressure
  3. dissolutionthe residue was dissolved in water
  4. washthe aqueous solution was washed with diethylether (3 times)
  5. additionThe pH of the aqueous solution was adjusted between 2 and 3 by addition of a solution of hydrochloric acid 6N
  6. filtrationthe formed precipitate was collected by filtration
  7. customPurification by preparative HPLC (HPLC method 4)

Sources & evidence

ORD record
ord-4ca0ca58d53b4d59b54a260ce47bcc28
Source dataset
uspto-grants-2014_12
Patent number
US08906906B2

Reaction notes

Loading…