Sodium Hydroxide → HCID 22611864, compound

HRID 843740Notes

Reaction equation

HRID 843740 reaction equation
C[O:2][C:3](=[O:35])[CH2:4][CH2:5][NH:6][C:7]([CH:9]1[CH2:14][CH2:13][CH2:12][N:11]([C:15](=[O:34])[CH2:16][O:17][CH:18]2[CH2:23][CH2:22][N:21]([C:24]([O:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[O:25])[CH2:20][CH2:19]2)[CH2:10]1)=[O:8].[OH-].[Na+].OS([O-])(=O)=O.[K+]>CO.O.O1CCCC1>[CH2:27]([O:26][C:24]([N:21]1[CH2:22][CH2:23][CH:18]([O:17][CH2:16][C:15]([N:11]2[CH2:12][CH2:13][CH2:14][CH:9]([C:7]([NH:6][CH2:5][CH2:4][C:3]([OH:35])=[O:2])=[O:8])[CH2:10]2)=[O:34])[CH2:19][CH2:20]1)=[O:25])[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 516920Potassium bisulfateHCID 22611859HCID 22611859, compound

Product 1

HCID 22611864HCID 22611864, compoundYield 94.4%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of N-[l-{2-(1-benzyloxycarbonyl4-piperidyloxy)acetyl}-3-piperidylcarbonyl]-β-alanine methyl ester (1.33 g) in methanol (10 ml), H2O (10 ml) and tetrahydrofuran (10 ml) was added 1N NaOH (8.55 ml) under stirring at 0° C. After stirring at ambient temperature for 3 hours, the mixture was acidified with 10% KHSO4 aqueous solution, and extracted with ethyl acetate. The extract was washed with water and brine, and dried over MgSO4, and evaporated in vacuo to give N-[1-{2-(1-benzyloxycarbonyl-4-piperidyloxy)acetyl}-3-piperidylcarbonyl]-β-alanine (1.22 g) as an oil.

Workup

  1. stirringAfter stirring at ambient temperature for 3 hours
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water and brine
  4. dry with materialdried over MgSO4
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-da0c39e1c7994cb586ab966241632265
Source dataset
uspto-grants-2002_04
Patent number
US06380215B1

Reaction notes

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