Lithium Hydroxide → HCID 22611806, compound

HRID 843741Notes

Reaction equation

HRID 843741 reaction equation
C[O:2][C:3](=[O:32])[CH2:4][CH2:5][NH:6][C:7]([CH:9]1[CH2:14][CH2:13][CH2:12][N:11]([C:15](=[O:31])[CH2:16][CH2:17][CH:18]2[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH2:19]2)[CH2:10]1)=[O:8].[OH-].[Li+].OS([O-])(=O)=O.[K+]>CO.O>[C:27]([O:26][C:24]([N:21]1[CH2:20][CH2:19][CH:18]([CH2:17][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:32])=[O:2])=[O:8])[CH2:10]2)=[O:31])[CH2:23][CH2:22]1)=[O:25])([CH3:30])([CH3:28])[CH3:29]

Participants

6

Reactant 3

HCID 3939Lithium HydroxideHCID 516920Potassium bisulfateHCID 22611994HCID 22611994, compound

Product 1

HCID 22611806HCID 22611806, compoundYield 82.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A solution of N-[1-{3-(1-tert-butoxycarbonyl-4-piperidyl)propionyl}-3-piperidylcarbonyl]-β-alanine methyl ester (2.03 g) in methanol (10 ml) and water (10 ml) was added lithium hydroxide (0.56 g) under stirring at 0° C. After stirring at ambient temperature for 1 hour, the mixture was acidified with 5% KHSO4 aqueous solution and extracted with ethyl acetate. The extract was washed with water, brine and dried over MgSO4, and evaporated in vacuo to give N-[1-{3-(1-tert-butoxycarbonyl-4-piperidyl)propionyl}-3-piperidylcarbonyl]-β-alanine as an oil (1.62 g).

Workup

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

Sources & evidence

ORD record
ord-14a9b503aebf49f08451fe6d1522b0ea
Source dataset
uspto-grants-2002_04
Patent number
US06380215B1

Reaction notes

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