Sodium Hydroxide → N-[3-(4-carboxybutoxy)-5-(octadecyloxy)phenyl]-N-(carboxymethyl)glycine

HRID 1110256Notes

Reaction equation

HRID 1110256 reaction equation
[C:1]([CH2:4][N:5]([C:10]1[CH:15]=[C:14]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]([O:23]C)=[O:22])[CH:13]=[C:12]([O:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])[CH:11]=1)[CH2:6][C:7]([OH:9])=[O:8])([OH:3])=[O:2].[OH-].[Na+]>CO>[C:21]([CH2:20][CH2:19][CH2:18][CH2:17][O:16][C:14]1[CH:15]=[C:10]([N:5]([CH2:4][C:1]([OH:3])=[O:2])[CH2:6][C:7]([OH:9])=[O:8])[CH:11]=[C:12]([O:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])[CH:13]=1)([OH:23])=[O:22]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19389036N-(carboxymethyl)-N-[3-(octadecyloxy)-5-[(5-methoxy-5-oxopentyl)oxy]phenyl]glycine

Product 1

HCID 19388986N-[3-(4-carboxybutoxy)-5-(octadecyloxy)phenyl]-N-(carboxymethyl)glycineYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2.0 g (3.3 mmol) of N-(carboxymethyl)-N-[3-(octadecyloxy)-5-[(5-methoxy-5-oxopentyl)oxy]phenyl]glycine and 2.8 ml (16.5 mmol) of 6N NaOH in 100 ml of methanol was stirred at reflux under argon for 16 hours. After cooling to room temperature, the precipitated sodium salt was removed by filtration, dissolved in 300 ml of water and the mixture was acidified with 4 ml of 6N HCl. The product was extracted with ethyl acetate and the dried extract was concentrated at reduced pressure to a solid which was recrystallized from acetone-hexane to give 1.8 g (92% yield, mp 126°-128°) of N-[3-(4-carboxybutoxy)-5-(octadecyloxy)phenyl]-N-(carboxymethyl)glycine.

Workup

  1. temperatureat reflux under argon for 16 hours
  2. customthe precipitated sodium salt was removed by filtration
  3. dissolutiondissolved in 300 ml of water
  4. extractionThe product was extracted with ethyl acetate
  5. extractionthe dried extract
  6. concentrationwas concentrated at reduced pressure to a solid which
  7. customwas recrystallized from acetone-hexane

Sources & evidence

ORD record
ord-527841ae6c634e54b73e00ed44fff4ba
Source dataset
uspto-grants-1994_06
Patent number
US05324747

Reaction notes

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