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

HRID 905280Notes

Reaction equation

HRID 905280 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-8b981c380e364b0b89f9937046d1f940
Source dataset
uspto-grants-1983_12
Patent number
US04423051

Reaction notes

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