Potassium Hydroxide → HCID 57513829, compound

HRID 2368415Notes

Reaction equation

HRID 2368415 reaction equation
C([O:3][C:4]([C:6]1[S:10][C:9]([NH:11][C:12](=[O:26])[C:13]([NH:16][C:17](=[O:25])[C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)([CH3:15])[CH3:14])=[N:8][C:7]=1[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:5])C.[OH-].[K+]>C1COCC1.C(O)C>[F:24][C:21]1[CH:20]=[CH:19][C:18]([C:17]([NH:16][C:13]([CH3:14])([CH3:15])[C:12]([NH:11][C:9]2[S:10][C:6]([C:4]([OH:5])=[O:3])=[C:7]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[N:8]=2)=[O:26])=[O:25])=[CH:23][CH:22]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 57513828HCID 57513828, compound

Product 1

HCID 57513829HCID 57513829, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 2-[2-(4-Fluoro-benzoylamino)-2-methyl-propionylamino]-4-phenyl-thiazole-5-carboxylic acid ethyl ester (357 mg, 0.785 mmol) and concentrated aqueous KOH (2 mL) in a mixture of THF (3 mL) and ethanol (5 mL) was heated at 65° C. for 2 h, cooled to RT and partitioned between ethyl acetate and 3 M HCl. The combined organic extract was dried and concentrated to give the title compound. m/z 428.1 (MH+).

Workup

  1. temperaturecooled to RT
  2. custompartitioned between ethyl acetate and 3 M HCl
  3. extractionThe combined organic extract
  4. customwas dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-56004f8dfa7b4944877ab7f0abdd6192
Source dataset
uspto-grants-2014_04
Patent number
US08703761B2

Reaction notes

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