Citric Acid → HCID 86674533, compound

HRID 1615402Notes

Reaction equation

HRID 1615402 reaction equation
C([O:3][C:4](=[O:27])[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:18][CH2:17][CH:16]([NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:15][CH2:14]2)=[CH:9][CH:8]=1)C.[OH-].[Na+].O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(O)C>[C:23]([O:22][C:20]([NH:19][CH:16]1[CH2:15][CH2:14][N:13]([C:10]2[CH:9]=[CH:8][C:7]([CH:6]=[CH:5][C:4]([OH:27])=[O:3])=[CH:12][CH:11]=2)[CH2:18][CH2:17]1)=[O:21])([CH3:26])([CH3:24])[CH3:25]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 86674531HCID 86674531, compound

Product 1

HCID 86674533HCID 86674533, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The 4-(4-tert-butoxycarbonylaminopiperidin-1-yl)-cinnamic acid ethyl ester (2.7 g, 7.2 mmol) obtained in Example 8(1) was dissolved in ethanol (40 ml), and a 4M sodium hydroxide aqueous solution (3.6 ml) was added thereto. The mixture was refluxed under heat for 12 hours. The reaction mixture was cooled to room temperature, and water (40 ml) was added thereto. The mixture was neutralized with 10% citric acid aqueous solution, and the precipitate was collected by filtration, thereby obtaining 4-(4-tert-butoxycarbonylaminopiperidin-1-yl)-cinnamic acid (1.9 g, 77%) as a white solid.

Workup

  1. temperatureThe mixture was refluxed
  2. temperatureunder heat for 12 hours
  3. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-172b02040b0a46bc876686bf9d255426
Source dataset
uspto-grants-2014_07
Patent number
US08765750B2

Reaction notes

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