Sodium Hydroxide → HCID 52937955, compound

HRID 1626784Notes

Reaction equation

HRID 1626784 reaction equation
C([O:3][C:4](=[O:38])[CH2:5][NH:6][C:7]([C:9]1[C:14]([OH:15])=[C:13]([CH3:16])[N:12]=[C:11]([CH2:17][CH:18]2[CH2:23][CH2:22][N:21]([C:24]3[CH:29]=[CH:28][C:27]([C:30]4[CH:35]=[CH:34][C:33]([CH2:36][OH:37])=[CH:32][CH:31]=4)=[CH:26][CH:25]=3)[CH2:20][CH2:19]2)[N:10]=1)=[O:8])C.[OH-].[Na+]>CO.O1CCCC1>[OH:15][C:14]1[C:9]([C:7]([NH:6][CH2:5][C:4]([OH:38])=[O:3])=[O:8])=[N:10][C:11]([CH2:17][CH:18]2[CH2:23][CH2:22][N:21]([C:24]3[CH:25]=[CH:26][C:27]([C:30]4[CH:35]=[CH:34][C:33]([CH2:36][OH:37])=[CH:32][CH:31]=4)=[CH:28][CH:29]=3)[CH2:20][CH2:19]2)=[N:12][C:13]=1[CH3:16]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 68196362HCID 68196362, compound

Product 1

HCID 52937955HCID 52937955, compoundYield 83.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl({[5-hydroxy-2-({1-[4′-(hydroxymethyl)biphenyl-4-yl]piperidin-4-yl}methyl)-6-methylpyrimidin-4-yl]carbonyl}amino)acetate (0.22 g, 0.42 mmol) was dissolved in a mixed solvent of methanol (5 mL) and tetrahydrofuran (5 mL), and an aqueous sodium hydroxide solution (1 M, 5.0 mL) was added, followed by stirring at room temperature for 30 minutes. The reaction solution was concentrated under reduced pressure, and hydrochloric acid (1 M, 5.0 mL) was added to the resulting residue, whereby a solid was deposited. The resulting solid was collected by filtration, and dried under reduced pressure to afford the title compound (0.17 g, 0.35 mmol) as a pale yellowish white solid (yield 82%).

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure, and hydrochloric acid (1 M, 5.0 mL)
  2. additionwas added to the resulting residue, whereby a solid
  3. filtrationThe resulting solid was collected by filtration
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-f53b28d69be842e983aa7ca533e68502
Source dataset
uspto-grants-2014_07
Patent number
US08785462B2

Reaction notes

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