Hydrochloric Acid → 2-{4-[2-(6-[(3-Chlorophenyl)(hydroxyimino)methyl]-2-oxo-1,3-benzothiazol-3(2H)-yl)ethoxy]phenoxy}-2-methylpropanoic acid

HRID 1790270Notes

Reaction equation

HRID 1790270 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8](=[N:37][OH:38])[C:9]2[CH:36]=[CH:35][C:12]3[N:13]([CH2:17][CH2:18][O:19][C:20]4[CH:34]=[CH:33][C:23]([O:24][C:25]([CH3:32])([CH3:31])[C:26]([O:28]CC)=[O:27])=[CH:22][CH:21]=4)[C:14](=[O:16])[S:15][C:11]=3[CH:10]=2)[CH:5]=[CH:6][CH:7]=1.[OH-].[K+].Cl>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:8](=[N:37][OH:38])[C:9]2[CH:36]=[CH:35][C:12]3[N:13]([CH2:17][CH2:18][O:19][C:20]4[CH:34]=[CH:33][C:23]([O:24][C:25]([CH3:32])([CH3:31])[C:26]([OH:28])=[O:27])=[CH:22][CH:21]=4)[C:14](=[O:16])[S:15][C:11]=3[CH:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 86596387Ethyl 2-{4-[2-(6-[(3-chlorophenyl)(hydroxyimino)methyl]-2-oxo-1,3-benzothiazol-3(2H)-yl)ethoxy]phenoxy}-2-methylpropanoate

Product 1

HCID 865963862-{4-[2-(6-[(3-Chlorophenyl)(hydroxyimino)methyl]-2-oxo-1,3-benzothiazol-3(2H)-yl)ethoxy]phenoxy}-2-methylpropanoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of the compound obtained in Example 37 (0.6 g) in 5 ml of ethanol 95° there is added potassium hydroxide (90 mg) dissolved in 1 ml of ethanol 95°. The reaction mixture is heated at reflux overnight. After cooling to ambient temperature, the solution is acidified using 1N HCl. The precipitate obtained is then filtered and purified on a reverse phase, RP18, eluant MeOH/H2O 6/4, to yield the title compound in the form of a white powder.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux overnight
  3. customThe precipitate obtained
  4. filtrationis then filtered
  5. custompurified on a reverse phase, RP18, eluant MeOH/H2O 6/4

Sources & evidence

ORD record
ord-b14af2bb85a04671a97996f852d4bdb4
Source dataset
uspto-grants-2006_07
Patent number
US07071221B2

Reaction notes

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