Sodium Hydroxide → N-(carboxymethyl)-N-(3,5-bis(decyloxy)-phenyl)glycine

HRID 1110215Notes

Reaction equation

HRID 1110215 reaction equation
C[O:2][C:3](=[O:39])[CH2:4][N:5]([CH2:34][C:35]([O:37]C)=[O:36])[C:6]1[CH:11]=[C:10]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH:9]=[C:8]([O:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH:7]=1.[OH-].[Na+]>CO>[C:3]([CH2:4][N:5]([C:6]1[CH:11]=[C:10]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH:9]=[C:8]([O:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH:7]=1)[CH2:34][C:35]([OH:37])=[O:36])([OH:39])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 15232831N-(2-methoxy-2-oxoethyl)-N-[3,5-bis(decyloxy) phenyl]glycine methyl ester

Product 1

HCID 192621N-(carboxymethyl)-N-(3,5-bis(decyloxy)-phenyl)glycineYield 31.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 0.205 g (0.373 mmol) of N-(2-methoxy-2-oxoethyl)-N-[3,5-bis(decyloxy)phenyl]glycine methyl ester and 1.5 ml (1.5 mmol) of 1.0N NaOH in 10 ml of methanol was stirred at reflux for 30 minutes. The solvent was removed under reduced pressure and the residue was acidified with 0.18 ml of acetic acid, the product was extracted with ethyl acetate and the dried extract was concentrated at reduced pressure to a solid. Recrystallization from methanol-water gave 61 mg (mp 110°-114°) of N-(carboxymethyl)-N-[3,5-bis(decyloxy)phenyl]glycine.

Workup

  1. temperatureat reflux for 30 minutes
  2. customThe solvent was removed under reduced pressure
  3. extractionthe product was extracted with ethyl acetate
  4. extractionthe dried extract
  5. concentrationwas concentrated at reduced pressure to a solid
  6. customRecrystallization from methanol-water

Sources & evidence

ORD record
ord-e39ec5253c8e4f8196339c2a105bbaa7
Source dataset
uspto-grants-1994_06
Patent number
US05324747

Reaction notes

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