Sodium Hydroxide → HCID 9830270, compound

HRID 275884Notes

Reaction equation

HRID 275884 reaction equation
C([O:3][C:4](=[O:46])[CH2:5][CH2:6][N:7]([CH2:35][C:36]1[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[C:38]([O:44][CH3:45])[CH:37]=1)[C:8](=[O:34])[CH2:9][N:10]([C:12](=[O:33])[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([NH:20][C:21]([NH:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[CH3:30])=[O:22])=[C:16]([O:31][CH3:32])[CH:15]=1)[CH3:11])C.[OH-].[Na+]>C(O)C>[CH3:45][O:44][C:38]1[CH:37]=[C:36]([CH:41]=[CH:40][C:39]=1[O:42][CH3:43])[CH2:35][N:7]([C:8](=[O:34])[CH2:9][N:10]([C:12](=[O:33])[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([NH:20][C:21]([NH:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[CH3:30])=[O:22])=[C:16]([O:31][CH3:32])[CH:15]=1)[CH3:11])[CH2:6][CH2:5][C:4]([OH:46])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57162964HCID 57162964, compound

Product 1

HCID 9830270HCID 9830270, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3-{(3,4-dimethoxy-benzyl)-[({[3-methoxy-4-(3-o-tolylureido)phenyl]-acetyl}-N-methylamino)-acetyl]-amino}-propionic acid ethyl ester [2.0 g, Reference Example 4(a)] in ethanol (50 ml) was treated with sodium hydroxide (3.5 ml, 1M). After stirring at room temperature for 3 hours the mixture was concentrated to dryness. The residue was dissolved in water (12 ml) and the pH of the solution was adjusted to 1.0 by addition of concentrated hydrochloric acid (0.25 ml) and then extracted three times with dicliloromethiane. The resultant solid was collected and recrystallised twice from 20% aqueous isopropanol to give 3-{(3,4-dimethoxy-benzyl)-[({[3-methoxy-4-(3-o-tolylureido)phenyl]-acetyl}-N-methylamino)-acetyl]-amino}-propionic acid (Compound C) as a white solid (0.25 g,), m.p. 183-187° C.

Workup

  1. concentrationwas concentrated to dryness
  2. dissolutionThe residue was dissolved in water (12 ml)
  3. additionthe pH of the solution was adjusted to 1.0 by addition of concentrated hydrochloric acid (0.25 ml)
  4. extractionextracted three times with dicliloromethiane
  5. customThe resultant solid was collected
  6. customrecrystallised twice from 20% aqueous isopropanol

Sources & evidence

ORD record
ord-0c1105cb72da46abbc45aced810f48ba
Source dataset
uspto-grants-2002_03
Patent number
US06352977B1

Reaction notes

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