Sodium Hydroxide → HCID 131719115, compound

HRID 1757876Notes

Reaction equation

HRID 1757876 reaction equation
C[O:2][C:3](=[O:50])[CH2:4][N:5](CC(OC)=O)[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]([CH3:44])=[O:43])=[CH:38][CH:37]=2)[CH:7]=1.[OH-].[Na+]>CO>[CH3:44][S:42]([C:39]1[CH:38]=[CH:37][C:36]([O:35][CH2:34][CH2:33][CH2:32][O:31][C:8]2[CH:7]=[C:6]([NH:5][CH2:4][C:3]([OH:50])=[O:2])[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]=2)=[CH:41][CH:40]=1)=[O:43]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19388927N-(2-methoxy-2-oxoethyl)-N-[3-[3-[4-(methylsulfinyl)phenoxy]propoxy]-5-(octadecyloxy)phenyl]glycine methyl ester

Product 1

HCID 131719115HCID 131719115, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 0.73 g (1.02 mmol) of N-(2-methoxy-2-oxoethyl)-N-[3-[3-[4-(methylsulfinyl)phenoxy]propoxy]-5-(octadecyloxy)phenyl]glycine methyl ester and 0.68 ml (4.08 mmol) of 6N NaOH in 30 ml of methanol was stirred at reflux under argon for 4 hours. 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 acetone-hexane to give 0.57 g (82% yield, mp 124°-126°) of N-(carboxymethyl)-N-[3-[3-[4-(methylsulfinyl)phenoxy]propoxy]-5-(octadecyloxy)phenyl glycine.

Workup

  1. temperatureat reflux under argon for 4 hours
  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 acetone-hexane

Sources & evidence

ORD record
ord-5d363ad33c874aaaab8670f096ca9988
Source dataset
uspto-grants-1995_08
Patent number
US05446189

Reaction notes

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