Sodium Hydroxide → N-(carboxymethyl)-N-[3-(octadecyloxy)-5-[(2-quinolinyl)methoxy]phenyl]glycine

HRID 1110310Notes

Reaction equation

HRID 1110310 reaction equation
C[O:2][C:3](=[O:48])[CH2:4][N:5]([CH2:43][C:44]([O:46]C)=[O:45])[C:6]1[CH:11]=[C:10]([O:12][CH2:13][C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]=2)[CH:9]=[C:8]([O:24][CH2:25][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][CH3:42])[CH:7]=1.[OH-].[Na+]>CO>[C:3]([CH2:4][N:5]([C:6]1[CH:11]=[C:10]([O:12][CH2:13][C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]=2)[CH:9]=[C:8]([O:24][CH2:25][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][CH3:42])[CH:7]=1)[CH2:43][C:44]([OH:46])=[O:45])([OH:48])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19389004HCID 19389004, compound

Product 1

HCID 19389011N-(carboxymethyl)-N-[3-(octadecyloxy)-5-[(2-quinolinyl)methoxy]phenyl]glycineYield 70%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1.5 g (2.26 mmol) of N-(2-methoxy-2-oxoethyl)-N-[3-(octadecyloxy)-5-[(2-quinolinyl)methoxy]phenyl]glycine methyl ester and 2.0 ml (12 mmol) of 6 N NaOH in 80 ml of methanol was stirred at reflux for 4 hours. The solvent was removed at reduced pressure, the residue was acidified and the product was removed by filtration. Recrystallization from THF-acetone gave 1.0 g (70% yield, mp 172°-174°) of N-(carboxymethyl)-N-[3-(octadecyloxy)-5-[(2-quinolinyl)methoxy]phenyl]glycine.

Workup

  1. temperatureat reflux for 4 hours
  2. customThe solvent was removed at reduced pressure
  3. customthe product was removed by filtration
  4. customRecrystallization from THF-acetone

Sources & evidence

ORD record
ord-ca216eb1cf4d43febd410a80aaaf4d69
Source dataset
uspto-grants-1994_06
Patent number
US05324747

Reaction notes

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