Sodium Hydroxide → N-[4-(8-cyclohexyloctylamino)benzoyl]glycine

HRID 903419Notes

Reaction equation

HRID 903419 reaction equation
[CH:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][NH:15][C:16]2[CH:30]=[CH:29][C:19]([C:20]([NH:22][CH2:23][C:24]([O:26]CC)=[O:25])=[O:21])=[CH:18][CH:17]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+]>C(O)C>[CH:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][NH:15][C:16]2[CH:30]=[CH:29][C:19]([C:20]([NH:22][CH2:23][C:24]([OH:26])=[O:25])=[O:21])=[CH:18][CH:17]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 20475823Ethyl 4-(8-cyclohexyloctylamino)hippurate

Product 1

HCID 20475803N-[4-(8-cyclohexyloctylamino)benzoyl]glycine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 26.4 g. of ethyl N-[4-(8-cyclohexyloctylamino)benzoyl]glycinate, 110 ml. of 1 N sodium hydroxide solution; and 100 ml. of ethanol is stirred at ambient temperature for 2 hours and then partially evaporated. The aqueous solution is washed with diethyl ether, acidified with 6 N hydrochloric acid, and filtered. The white solid is dried in vacuo and recrystallized from acetone to yield the product.

Workup

  1. additionA mixture of 26.4 g
  2. custompartially evaporated
  3. washThe aqueous solution is washed with diethyl ether
  4. filtrationfiltered
  5. customThe white solid is dried in vacuo
  6. customrecrystallized from acetone
  7. customto yield the product

Sources & evidence

ORD record
ord-aabe78f552ce425bb304f78cd88e5380
Source dataset
uspto-grants-1980_10
Patent number
US04227014

Reaction notes

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