Sodium Hydroxide → HCID 53822982, compound

HRID 488277Notes

Reaction equation

HRID 488277 reaction equation
C([O:3][C:4](=[O:52])[CH2:5][N:6]([CH2:46][C:47]([O:49]CC)=[O:48])[C:7](=[O:45])[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22][O:23][CH2:24][CH3:25])[C:9]=1[O:26][CH:27]([CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])[CH2:28][CH2:29][CH2:30][CH3:31])C.[OH-].[Na+]>CO>[C:4]([CH2:5][N:6]([C:7](=[O:45])[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22][O:23][CH2:24][CH3:25])[C:9]=1[O:26][CH:27]([CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])[CH2:28][CH2:29][CH2:30][CH3:31])[CH2:46][C:47]([OH:49])=[O:48])([OH:52])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19091835HCID 19091835, compound

Product 1

HCID 53822982HCID 53822982, compoundYield 71.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1.0 g (1.36 mmol) of N-(2-ethoxy-2-oxoethyl)-N-[3-[2-[2-(2-ethoxyethoxy)ethoxy]ethoxy]-(5-octadecyloxy)benzoyl]glycine ethyl ester and 1.1 ml (6.6 mmol) of 6N NaOH in 25 ml of methanol was stirred at room temperature for 4 hours. The solvent was removed at reduced pressure, the residue was acidified and the product was extracted with ethyl acetate. The dried extract was concentrated to an oil which was purified by chromatography on 30 g of silica gel (230-400 mesh) using 25% methanol-chloroform to give 0.66 g (71% yield) of N-(carboxymethyl)-N-[3-[2-[2-(2-ethoxyethoxy)ethoxy]ethoxy]-(5-octadecyloxy)benzoyl]glycine as an oil. The structure was confirmed by nmr and mass spectra.

Workup

  1. customThe solvent was removed at reduced pressure
  2. extractionthe product was extracted with ethyl acetate
  3. extractionThe dried extract
  4. concentrationwas concentrated to an oil which
  5. customwas purified by chromatography on 30 g of silica gel (230-400 mesh)

Sources & evidence

ORD record
ord-c4ba7a40c24043b8bbcab9a9b001c4f0
Source dataset
uspto-grants-1994_03
Patent number
US05298652

Reaction notes

Loading…