Sodium Hydroxide → HCID 70170989, compound

HRID 275886Notes

Reaction equation

HRID 275886 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:40]=[CH:41][C:42]=1[O:43][CH3:44])[CH2:6][N:7]([C:13](=[O:39])[CH2:14][N:15]([C:17](=[O:38])[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([NH:25][C:26]([NH:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[CH3:35])=[O:27])=[C:21]([O:36][CH3:37])[CH:20]=1)[CH3:16])[CH2:8][CH2:9][C:10]([OH:12])=[O:11].[OH-].[Na+:46]>C(O)C>[Na+:46].[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:40]=[CH:41][C:42]=1[O:43][CH3:44])[CH2:6][N:7]([C:13](=[O:39])[CH2:14][N:15]([C:17](=[O:38])[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([NH:25][C:26]([NH:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[CH3:35])=[O:27])=[C:21]([O:36][CH3:37])[CH:20]=1)[CH3:16])[CH2:8][CH2:9][C:10]([O-:12])=[O:11]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 9830270HCID 9830270, compound

Product 1

HCID 70170989HCID 70170989, 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 [17 g, Example 5(a)] in ethanol (170 ml) was treated with sodium hydroxide solution (23.3 ml, 1N). After stirring at ambient temperature for 24 hours the reaction mixture was filtered through a short pad of diatomaceous earth and then evaporated. The residue was triturated with hot ethyl acetate (200 ml) and dried under vacuum. The resultant foam was dissolved in water (200 ml) and freeze dried for 40 hours to yield the title compound as a white solid (15.4 g), m.p. 225° C. (with decomposition). [Elemental analysis:- C,57.8; H,6.05; N,8.2; Na,3.5%. Calculated for C32H37N4NaO8.2H2O:- C,57.8; H,6.2; N,8.4; Na,3.5%].

Workup

  1. filtrationwas filtered through a short pad of diatomaceous earth
  2. customevaporated
  3. customThe residue was triturated with hot ethyl acetate (200 ml)
  4. customdried under vacuum
  5. dissolutionThe resultant foam was dissolved in water (200 ml)
  6. customfreeze dried for 40 hours

Sources & evidence

ORD record
ord-8507da3eb9e74f59800fde581c0347eb
Source dataset
uspto-grants-2002_03
Patent number
US06352977B1

Reaction notes

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