Sodium Hydroxide → HCID 19388924, compound

HRID 1757859Notes

Reaction equation

HRID 1757859 reaction equation
C([O:3][C:4](=[O:47])[CH2:5][CH2:6][N:7]([C:15]1[CH:20]=[C:19]([C:21]([NH:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])=[O:22])[CH:18]=[C:17]([C:34]([NH:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46])=[O:35])[CH:16]=1)CCC(OCC)=O)C.[OH-:48].[Na+]>CO>[C:4]([CH2:5][CH2:6][C:16]1[C:17]([C:34]([NH:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46])=[O:35])=[CH:18][C:19]([C:21]([NH:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])=[O:22])=[CH:20][C:15]=1[NH:7][CH2:6][CH2:5][C:4]([OH:3])=[O:47])([OH:3])=[O:48]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 54340834HCID 54340834, compound

Product 1

HCID 19388924HCID 19388924, compoundYield 123%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 0.23 g (0.35 mmol) of 3-[[3,5-bis[(decylamino)carbonyl]phenyl](3-ethoxy-3-oxopropyl)amino]propanoic acid ethyl ester and 1.4 ml (1.4 mmol) of 1N NaOH in 10 ml of methanol was stirred at room temperature for 16 hours. The solvent was removed at reduced pressure, the residue was dissolved in water and acidified with 0.2 ml of acetic acid. The precipitate was filtered and recrystallized from acetone-hexane to give 0.13 g (60% yield, mp 139°-141°)of 3-[[(2-carboxyethyl)-3,5-bis[(decylamino)carbonyl]phenyl]amino]propanoicacid.

Workup

  1. customThe solvent was removed at reduced pressure
  2. dissolutionthe residue was dissolved in water
  3. filtrationThe precipitate was filtered
  4. customrecrystallized from acetone-hexane

Sources & evidence

ORD record
ord-4c5770c738154007b1ac66860997a133
Source dataset
uspto-grants-1995_08
Patent number
US05446189

Reaction notes

Loading…