Sodium Hydroxide → HCID 19389052, compound

HRID 1757883Notes

Reaction equation

HRID 1757883 reaction equation
C[O:2][C:3](=[O:51])[CH2:4][N:5]([C:11]1[CH:16]=[C:15]([O: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][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH:14]=[C:13]([O:36][CH2:37][CH2:38][CH2:39][O:40][C:41]2[CH:46]=[CH:45][C:44]([C:47]([CH3:50])([CH3:49])[CH3:48])=[CH:43][CH:42]=2)[CH:12]=1)[CH2:6][C:7]([O:9]C)=[O:8].[OH-].[Na+].O1CCOCC1>CO>[C:3]([CH2:4][N:5]([C:11]1[CH:16]=[C:15]([O: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][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH:14]=[C:13]([O:36][CH2:37][CH2:38][CH2:39][O:40][C:41]2[CH:46]=[CH:45][C:44]([C:47]([CH3:48])([CH3:50])[CH3:49])=[CH:43][CH:42]=2)[CH:12]=1)[CH2:6][C:7]([OH:9])=[O:8])([OH:51])=[O:2]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 19389109N-[3-[3-[4-(1,1-dimethylethyl)phenoxy]propoxy]-5-(octadecyloxy)phenyl]-N-(2-methoxy-2-oxoethyl)glycine methyl ester

Product 1

HCID 19389052HCID 19389052, compoundYield 92.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 0.815 g (1.14 mmol) of N-[3-[3-[4-(1,1-dimethylethyl)phenoxy]propoxy]-5-(octadecyloxy)phenyl]-N-(2-methoxy-2-oxoethyl)glycine methyl ester and 0.76 mL of 6N NaOH in 20 mL of methanol-10 mL of dioxane was stirred at reflux under argon for 5 hours. The solvents were removed at reduced pressure, the residue was acidified with dilute HCl and the product was extracted with ethyl acetate. The dried extract was concentrated at reduced pressure and the residue was crystallized from methanol-water to give 0.72 g (92% yield, mp99°-101°) of N-(carboxymethyl)-N-[3-[3-[4-(1,1-dimethylethyl)phenoxy]propoxy]-5-(octadecyloxy) phenyl]glycine.

Workup

  1. temperatureat reflux under argon for 5 hours
  2. customThe solvents were removed at reduced pressure
  3. extractionthe product was extracted with ethyl acetate
  4. extractionThe dried extract
  5. concentrationwas concentrated at reduced pressure
  6. customthe residue was crystallized from methanol-water

Sources & evidence

ORD record
ord-4b9a0e33d7004a29a9d8cebeda64d644
Source dataset
uspto-grants-1995_08
Patent number
US05446189

Reaction notes

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