Sodium Hydroxide → HCID 19091862, compound

HRID 488303Notes

Reaction equation

HRID 488303 reaction equation
C([O:3][C:4](=[O:45])[CH2:5][N:6]([C:13](=[O:44])[C:14]([C:16]1[CH:21]=[C:20]([O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH:19]=[C:18]([O:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])[CH:17]=1)=[O:15])[CH2:7][C:8]([O:10]CC)=[O:9])C.[OH-].[Na+]>CO>[C:8]([CH2:7][N:6]([C:13](=[O:44])[C:14]([C:16]1[CH:21]=[C:20]([O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH:19]=[C:18]([O:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])[CH:17]=1)=[O:15])[CH2:5][C:4]([OH:45])=[O:3])([OH:10])=[O:9]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 54116100HCID 54116100, compound

Product 1

HCID 19091862HCID 19091862, compoundYield 87.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1.2 g (1.9 mmol) of N-[[3,5-bis(decyloxy)phenyl]-1,2-dioxoethyl]-N-(2-ethoxy-2-oxoethyl)glycine ethyl ester in 75 ml of methanol and 1.6 ml (9.6 mmol) of 6.0 N NaOH was stirred at reflux under argon for 4 hours. The solvent was removed at reduced pressure, the residue was treated with water and 2.5 ml of 6N HCl and the product was extracted with ethyl acetate. The dried extract was concentrated to a foam which was crystallized from hexane to give 0.96 g (87% yield, mp 76°-78°) of N-(carboxymethyl)-N-[[3,5-bis(decyloxy)phenyl]-1,2-dioxoethyl]glycine.

Workup

  1. temperatureat reflux under argon for 4 hours
  2. customThe solvent was removed at reduced pressure
  3. additionthe residue was treated with water and 2.5 ml of 6N HCl
  4. extractionthe product was extracted with ethyl acetate
  5. extractionThe dried extract
  6. concentrationwas concentrated to a foam which
  7. customwas crystallized from hexane

Sources & evidence

ORD record
ord-07d53f3b13d949c49aa43fcd6549d1eb
Source dataset
uspto-grants-1994_03
Patent number
US05298652

Reaction notes

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