Hydrochloric Acid → N-[3-carboxy-5-(octadecyloxy)phenyl]-N-(carboxymethyl)glycine

HRID 1110261Notes

Reaction equation

HRID 1110261 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][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[CH:13]=[C:12]([C:35]([O:37]C)=[O:36])[CH:11]=1)[CH2:6][C:7]([OH:9])=[O:8])([OH:3])=[O:2].[OH-].[Na+].Cl.O>CO>[C:35]([C:12]1[CH:11]=[C:10]([N:5]([CH2:4][C:1]([OH:3])=[O:2])[CH2:6][C:7]([OH:9])=[O:8])[CH:15]=[C:14]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[CH:13]=1)([OH:37])=[O:36]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 19388921N-(carboxymethyl)-N-[3-(methoxy-carbonyl)-5-(octadecyloxy)phenyl]glycine

Product 1

HCID 19389145N-[3-carboxy-5-(octadecyloxy)phenyl]-N-(carboxymethyl)glycineYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1.0 g (1.87 mmol) of N-(carboxymethyl)-N-[3(methoxycarbonyl)-5-(octadecyloxy)phenyl]glycine and 3.1 ml (9.35 mmol) of 3N NaOH in 100 ml of methanol was stirred at reflux under argon for 48 hours. The warm solution was acidified with 3N HCl to pH 2 and the methanol was removed at reduced pressure. Water was added and the product was filtered and recrystallized from methanol-water to give 0.78 g (80% yield, mp 149°-155°) of N-[3-carboxy-5-(octadecyloxy)phenyl]-N-(carboxymethyl)glycine as a hydrate with 0.75 mole of water.

Workup

  1. temperatureat reflux under argon for 48 hours
  2. customthe methanol was removed at reduced pressure
  3. additionWater was added
  4. filtrationthe product was filtered
  5. customrecrystallized from methanol-water

Sources & evidence

ORD record
ord-c2bf5a0e1740486a8c2842a127f3c1bd
Source dataset
uspto-grants-1994_06
Patent number
US05324747

Reaction notes

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