Sodium Hydroxide → HCID 19389122, compound

HRID 1110312Notes

Reaction equation

HRID 1110312 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][CH2:14][O:15][CH2:16][CH2:17][O:18][CH2:19][CH2:20][O:21][CH2:22][CH3:23])[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:44]([CH2:43][N:5]([C:6]1[CH:7]=[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:9]=[C:10]([O:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][O:18][CH2:19][CH2:20][O:21][CH2:22][CH3:23])[CH:11]=1)[CH2:4][C:3]([OH:48])=[O:2])([OH:46])=[O:45]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19389072N-(2-methoxy-2-oxoethyl)-N-[3-octadecyloxy-5-(3,6,9-trioxaundec-1-yloxy)phenyl]glycine methyl ester

Product 1

HCID 19389122HCID 19389122, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1.76 g (2.58 mmol) of N-(2-methoxy-2-oxoethyl)-N-[3-octadecyloxy-5-(3,6,9-trioxaundec-1-yloxy)phenyl]glycine methyl ester and 2.2 ml (12.9 mmol) of 6 N NaOH in 75 ml of methanol was kept at room temperature for 70 hours. The solvent was removed at reduced pressure and the residue was acidified to pH 2. The product was extracted with ethyl acetate and the dried extract was concentrated at reduced pressure to a solid which was triturated with hexane and filtered to give 1.62 g (96% yield, mp 76°-78°) of N-[(Carboxymethyl)-N-[3-[2-[2-(2-ethoxyethoxy)ethoxy]ethoxy]-5-(octadecyloxy)phenyl]glycine.

Workup

  1. customThe solvent was removed at reduced pressure
  2. extractionThe product was extracted with ethyl acetate
  3. extractionthe dried extract
  4. concentrationwas concentrated at reduced pressure to a solid which
  5. customwas triturated with hexane
  6. filtrationfiltered

Sources & evidence

ORD record
ord-5f4bc132284043adb4897148dc9c58b7
Source dataset
uspto-grants-1994_06
Patent number
US05324747

Reaction notes

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