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

HRID 1757821Notes

Reaction equation

HRID 1757821 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 82.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1.0 g (1.81 mmol) of N-(carboxymethyl)-N-[3(methoxycarbonyl)-5-(octadecyloxy)phenyl]glycine and3.1 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 andthe 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 hydratewith 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 andthe product
  4. filtrationwas filtered
  5. customrecrystallized from methanol-water

Sources & evidence

ORD record
ord-c1f20cc04218470d898dcf4a179b11fe
Source dataset
uspto-grants-1995_08
Patent number
US05446189

Reaction notes

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