Sodium Hydroxide → N-(carboxymethyl)-N-[3-[3-[4-(methylsulfonyl)phenoxy]propoxy]-5-(octadecyloxy)phenyl]glycine

HRID 1110315Notes

Reaction equation

HRID 1110315 reaction equation
C[O:2][C:3](=[O:51])[CH2:4][N:5]([CH2:46][C:47]([O:49]C)=[O:48])[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][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH:9]=[C:8]([O:31][CH2:32][CH2:33][CH2:34][O:35][C:36]2[CH:41]=[CH:40][C:39]([S:42]([CH3:45])(=[O:44])=[O:43])=[CH:38][CH:37]=2)[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][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH:9]=[C:8]([O:31][CH2:32][CH2:33][CH2:34][O:35][C:36]2[CH:41]=[CH:40][C:39]([S:42]([CH3:45])(=[O:43])=[O:44])=[CH:38][CH:37]=2)[CH:7]=1)[CH2:46][C:47]([OH:49])=[O:48])([OH:51])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19389016HCID 19389016, compound

Product 1

HCID 19388944N-(carboxymethyl)-N-[3-[3-[4-(methylsulfonyl)phenoxy]propoxy]-5-(octadecyloxy)phenyl]glycineYield 86.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1.01 g (1.37 mmol) of N-(2-methoxy-2-oxoethyl)-N-[3-[3-[4-(methylsulfonyl) phenoxy]propoxy]-5-(octadecyloxy)-phenyl]glycine methyl ester and 0.92 ml (5.5 mmol) of 6 N NaOH in 30 ml of methanol was stirred at reflux for 4 hours under argon. The methanol was removed at reduced pressure, the residue was acidified and the product was extracted with ethyl acetate. The dried extract was concentrated to a solid which was recrystallized from methylene chloride-ether to give 0.835 g (86% yield, mp 118°-120°) of N-(carboxymethyl)-N-[3-[3-[4-(methylsulfonyl)phenoxy]propoxy]-5-(octadecyloxy)phenyl]glycine.

Workup

  1. temperatureat reflux for 4 hours under argon
  2. customThe methanol was removed at reduced pressure
  3. extractionthe product was extracted with ethyl acetate
  4. extractionThe dried extract
  5. concentrationwas concentrated to a solid which
  6. customwas recrystallized from methylene chloride-ether

Sources & evidence

ORD record
ord-d3a2dd9b3e7040ebb4fe7710df84a692
Source dataset
uspto-grants-1994_06
Patent number
US05324747

Reaction notes

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