Sodium Hydroxide → HCID 19389103, compound

HRID 1757797Notes

Reaction equation

HRID 1757797 reaction equation
C[O:2][C:3](=[O:36])[CH2:4][N:5]([CH2:31][C:32]([O:34]C)=[O:33])[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][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][CH3:30])[CH:7]=1.[OH-].[Na+]>CO>[C:3]([CH2:4][N:5]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][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][CH3:30])[CH:7]=1)[CH2:31][C:32]([OH:34])=[O:33])([OH:36])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19389057HCID 19389057, compound

Product 1

HCID 19389103HCID 19389103, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 0.56 g (1.11 mmol) of N-(2-methoxy-2-oxoethyl)-N-[3-(octadecyloxy)phenyl]glycine methyl ester and 4.4 ml (4.4 mmol) of 1N NaOH in 50 ml of methanol was stirred at reflux under an talon atmosphere for 75 minutes. After standing at room temperature for 17 hours the precipitate was removed by filtration. The solid was suspended in 100 ml of 1N HCl and extracted with ethyl acetate. The dried extract was concentrated at reduced pressure and the resultant solid was recrystallized from methanol-water to give 0.31 g (60% yield, mp135°-138°) of N-(carboxymethyl)-N-[3-(octadecyloxy)phenyl]glycine.

Workup

  1. temperatureat reflux under an talon atmosphere for 75 minutes
  2. customthe precipitate was removed by filtration
  3. extractionextracted with ethyl acetate
  4. extractionThe dried extract
  5. concentrationwas concentrated at reduced pressure
  6. customthe resultant solid was recrystallized from methanol-water

Sources & evidence

ORD record
ord-1d29396aaa404ea68f979abb8bd6e9e1
Source dataset
uspto-grants-1995_08
Patent number
US05446189

Reaction notes

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