Sodium Hydroxide → HCID 50995181, compound

HRID 1399618Notes

Reaction equation

HRID 1399618 reaction equation
[OH-].[Na+].[CH3:3][C:4]1[C:9]([CH:10]([CH2:15][CH2:16][CH3:17])[C:11]([O:13]C)=[O:12])=[C:8]([C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)[N:7]=[C:6]([N:25]2[CH2:30][CH2:29][CH2:28][CH:27]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH2:26]2)[N:5]=1>CO>[CH3:3][C:4]1[C:9]([CH:10]([CH2:15][CH2:16][CH3:17])[C:11]([OH:13])=[O:12])=[C:8]([C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)[N:7]=[C:6]([N:25]2[CH2:30][CH2:29][CH2:28][CH:27]([C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)[CH2:26]2)[N:5]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 50995369HCID 50995369, compound

Product 1

HCID 50995181HCID 50995181, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

A solution of sodium hydroxide 5N (0.5 mL) was added to a mixture of methyl 2-(4-methyl-2-(3-phenylpiperidin-1-yl)-6-p-tolylpyrimidin-5-yl)pentanoate (0.047 g; 0.103 mmol) in methanol (1.5 mL). The mixture was heated in a sealed tube at 100° C. for 18 h and then concentrated under reduced pressure. The residue was dissolved in water and the pH of the solution was adjusted between 3 and 4 by addition of a solution of hydrochloric acid 6N. The aqueous layer was extracted with ethyl acetate, dried over sodium sulphate, filtered and concentrated under reduced pressure. Purification by preparative HPLC (HPLC method 4) furnished 0.014 g (31%) of the title compound as a white solid.

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue was dissolved in water
  3. additionthe pH of the solution was adjusted between 3 and 4 by addition of a solution of hydrochloric acid 6N
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customPurification by preparative HPLC (HPLC method 4)

Sources & evidence

ORD record
ord-b28078883c8948738826e9139a591039
Source dataset
uspto-grants-2014_12
Patent number
US08906906B2

Reaction notes

Loading…