HCID 86645979, compound → HCID 86645980, compound

HRID 1094327Notes

Reaction equation

HRID 1094327 reaction equation
[O:1]=[C:2]([C@@H:8]([C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17]2[S:18][CH:19]=[C:20]([C:22]([F:25])([F:24])[F:23])[N:21]=2)=[CH:12][CH:11]=1)[CH3:9])[CH2:3][C:4]([O:6]C)=[O:5]>CC(O)=O.Cl>[O:1]=[C:2]([C@@H:8]([C:10]1[CH:11]=[CH:12][C:13]([NH:16][C:17]2[S:18][CH:19]=[C:20]([C:22]([F:25])([F:24])[F:23])[N:21]=2)=[CH:14][CH:15]=1)[CH3:9])[CH2:3][C:4]([OH:6])=[O:5]

Participants

4

Reactant 1

HCID 86645979HCID 86645979, compound

Product 1

HCID 86645980HCID 86645980, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolvent

Procedure

A solution of methyl (4R)-3-oxo-4-(4-{[4-(trifluoromethyl)-1,3-thiazol-2-yl]amino}phenyl)pentanoate (372 mg, 1 mmol) in AcOH (10 ml) and 37% HCl (1.5 ml) was refluxed for 12 h. After cooling at room temperature and solvents evaporation, the crude product was diluted with CH2Cl2 (10 ml), washed with water (3×5 ml) and brine (3×5 ml) and dried over anhydrous Na2SO4. After solvent evaporation the resulting pale yellow oil was pulped overnight in n-hexane. Pure (4R)-3-oxo-4-(4-{[4-(trifluoromethyl)-1,3-thiazol-2-yl]amino}phenyl)pentanoic acid (283 mg, 0.79 mmol) was isolated as a white solid by filtration (79%).

Workup

  1. customsolvents evaporation
  2. additionthe crude product was diluted with CH2Cl2 (10 ml)
  3. washwashed with water (3×5 ml) and brine (3×5 ml)
  4. dry with materialdried over anhydrous Na2SO4
  5. customAfter solvent evaporation the resulting pale yellow oil

Sources & evidence

ORD record
ord-177482009e2447a3b875cee1e5add898
Source dataset
uspto-grants-2012_03
Patent number
US08133911B2

Reaction notes

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