Hydrochloric Acid → 3-{3-[5-(4-Dimethylsulfamoyl-phenyl)-4-methyl-thiazol-2-yl]-ureido}-propionic acid

HRID 1093008Notes

Reaction equation

HRID 1093008 reaction equation
C([O:3][C:4](=[O:29])[CH2:5][CH2:6][NH:7][C:8]([NH:10][C:11]1[S:12][C:13]([C:17]2[CH:22]=[CH:21][C:20]([S:23](=[O:28])(=[O:27])[N:24]([CH3:26])[CH3:25])=[CH:19][CH:18]=2)=[C:14]([CH3:16])[N:15]=1)=[O:9])C.[OH-].[Na+].Cl>CO>[CH3:26][N:24]([CH3:25])[S:23]([C:20]1[CH:21]=[CH:22][C:17]([C:13]2[S:12][C:11]([NH:10][C:8](=[O:9])[NH:7][CH2:6][CH2:5][C:4]([OH:29])=[O:3])=[N:15][C:14]=2[CH3:16])=[CH:18][CH:19]=1)(=[O:27])=[O:28]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 865984013-{3-[5-(4-Dimethylsulfamoyl-phenyl)-4-methyl-thiazol-2-yl]-ureido}-propionic acid ethyl ester

Product 1

HCID 865984413-{3-[5-(4-Dimethylsulfamoyl-phenyl)-4-methyl-thiazol-2-yl]-ureido}-propionic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 3-{3-[5-(4-dimethylsulfamoyl-phenyl)-4-methyl-thiazol-2-yl]-ureido}-propionic acid ethyl ester (Example 24) in methanol (5 ml) is added dropwise sodium hydroxide (2M, 3 ml) over 2 minutes. The reaction mixture is heated at reflux overnight and then allowed to cool to room temperature. The mixture is neutralised with hydrochloric acid (2M, 3 ml) and the resulting precipitate is filtered, washed with water (20 ml) and dried in vacuo to yield the titled compound.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux overnight
  3. filtrationthe resulting precipitate is filtered
  4. washwashed with water (20 ml)
  5. customdried in vacuo

Sources & evidence

ORD record
ord-cb6106f0404f482f87218c94887b0c84
Source dataset
uspto-grants-2012_03
Patent number
US08129541B2

Reaction notes

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