Sodium Hydroxide → HCID 50995183, compound

HRID 1399616Notes

Reaction equation

HRID 1399616 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]([O:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=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]([O:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH2:26]2)[N:5]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 50995368HCID 50995368, compound

Product 1

HCID 50995183HCID 50995183, compoundYield 53.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

A solution of sodium hydroxide 5N (1 mL) was added to a mixture of methyl 2-(4-methyl-2-(3-phenoxypiperidin-1-yl)-6-p-tolylpyrimidin-5-yl)pentanoate (0.050 g; 0.053 mmol) in methanol (1 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 2 and 3 by addition of a solution of hydrochloric acid 6N. The aqueous layer was extracted with ethyl acetate, dried and concentrated under reduced pressure. Purification by preparative HPLC (HPLC method 4) furnished 0.013 g (26%) 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 2 and 3 by addition of a solution of hydrochloric acid 6N
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customPurification by preparative HPLC (HPLC method 4)

Sources & evidence

ORD record
ord-d146c803873e4c8f80a0a6c874998506
Source dataset
uspto-grants-2014_12
Patent number
US08906906B2

Reaction notes

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