Hydrochloric Acid → HCID 66939389, compound

HRID 1257365Notes

Reaction equation

HRID 1257365 reaction equation
C([O:4][CH2:5][C:6]([NH:8][C:9]1[CH:10]=[C:11]([C:15]2[N:16]=[C:17]([CH2:20][N:21]3[CH:25]=[C:24]([C:26]([O:28]CC)=[O:27])[CH:23]=[N:22]3)[S:18][CH:19]=2)[CH:12]=[CH:13][CH:14]=1)=[O:7])(=O)C.[OH-].[Na+].Cl>C(O)C.[Cl-].[Na+].O>[OH:4][CH2:5][C:6]([NH:8][C:9]1[CH:10]=[C:11]([C:15]2[N:16]=[C:17]([CH2:20][N:21]3[CH:25]=[C:24]([C:26]([OH:28])=[O:27])[CH:23]=[N:22]3)[S:18][CH:19]=2)[CH:12]=[CH:13][CH:14]=1)=[O:7]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66939480ethyl 1-{[4-(3-{[(acetyloxy)acetyl]amino}phenyl)-1,3-thiazol-2-yl]methyl}-1H-pyrazole-4-carboxylate

Product 1

HCID 66939389HCID 66939389, compoundYield 48.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution (4 mL) of the compound (270 mg, 0.63 mmol) obtained in Example 45a in ethanol was added 2N aqueous sodium hydroxide solution (1.7 mL, 3.4 mmol), and the mixture was stirred at room temperature overnight. The reaction mixture was neutralized with 1N aqueous hydrochloric acid solution, saturated brine was added, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The resulting crude title compound was recrystallized (tetrahydrofuran-ethyl acetate-hexane) to give the title compound (110 mg, 33%) as colorless crystals.

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe obtained organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customThe resulting crude title compound was recrystallized (tetrahydrofuran-ethyl acetate-hexane)

Sources & evidence

ORD record
ord-5398be2d458343989c1b01455782f7cc
Source dataset
uspto-grants-2013_06
Patent number
US08461348B2

Reaction notes

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