Water → Z-2-(2-Aminothiazol-4-yl)-2-butenoic acid

HRID 2231374Notes

Reaction equation

HRID 2231374 reaction equation
[OH-].[K+].O.C([NH:7][C:8]1[S:9][CH:10]=[C:11](/[C:13](=[CH:19]/[CH3:20])/[C:14]([O:16]CC)=[O:15])[N:12]=1)(=O)C.FC(F)(F)C(O)=O>CC(C)=O>[NH2:7][C:8]1[S:9][CH:10]=[C:11](/[C:13](=[CH:19]/[CH3:20])/[C:14]([OH:16])=[O:15])[N:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 14797Potassium HydroxideHCID 13603194Ethyl Z-2-(2-acetamidothiazol-4-yl)-2-butenoate

Product 1

HCID 13561558Z-2-(2-Aminothiazol-4-yl)-2-butenoic acid

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
10 °C

Procedure

A solution of 16.5 parts by weight of potassium hydroxide in 111 parts by volume of water is heated up to 75° to 78° C. 14.9 parts by weight of ethyl Z-2-(2-acetamidothiazol-4-yl)-2-butenoate are added and the mixture is stirred at 75° to 78° C. for 2 hours. After cooling to 10° C., the mixture is brought to pH 7.0 with trifluoroacetic acid, the solution is filtered with suction over kieselguhr and the pH is then brought to 3.6 with further trifluoroacetic acid. The mixture is cooled to 0° C. and stirred at 0° C. for 30 minutes, and the crystals which have precipitated are isolated. After washing three times with 6 parts by volume of isopropanol each time, the crystals are dried. The product is then stirred with 62.4 parts by volume of acetone for 20 minutes, filtered off with suction, washed with 42 parts by volume of acetone and dried again. 6.3 parts by weight of pure product are obtained. Further product can be isolated from the mother liquor of the acetone extraction stirring.

Workup

  1. filtrationthe solution is filtered with suction over kieselguhr
  2. temperatureThe mixture is cooled to 0° C.
  3. stirringstirred at 0° C. for 30 minutes
  4. customthe crystals which have precipitated
  5. customare isolated
  6. washAfter washing three times with 6 parts by volume of isopropanol each time
  7. customthe crystals are dried
  8. stirringThe product is then stirred with 62.4 parts by volume of acetone for 20 minutes
  9. filtrationfiltered off with suction
  10. washwashed with 42 parts by volume of acetone
  11. customdried again
  12. custom6.3 parts by weight of pure product are obtained
  13. stirringstirring

Sources & evidence

ORD record
ord-f49ced6daa83439782ba3b05b89516b2
Source dataset
uspto-grants-1988_11
Patent number
US04782162

Reaction notes

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