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

HRID 1757776Notes

Reaction equation

HRID 1757776 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 61mg (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. extractionwas 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-30f12905a5bf46fda5670e92d22af43f
Source dataset
uspto-grants-1995_08
Patent number
US05446189

Reaction notes

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