Hydrochloric Acid → 5-[5-(5-Chloro-2-hydroxy-phenyl)-oxazol-2-yl]-pentanoic acid

HRID 1039201Notes

Reaction equation

HRID 1039201 reaction equation
C[O:2][C:3](=[O:21])[CH2:4][CH2:5][CH2:6][CH2:7][C:8]1[O:9][C:10]([C:13]2[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=2[OH:20])=[CH:11][N:12]=1.[Li+].[OH-].Cl>O1CCOCC1.O>[Cl:19][C:17]1[CH:16]=[CH:15][C:14]([OH:20])=[C:13]([C:10]2[O:9][C:8]([CH2:7][CH2:6][CH2:5][CH2:4][C:3]([OH:21])=[O:2])=[N:12][CH:11]=2)[CH:18]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 684878995-[5-(5-Chloro-2-hydroxy-phenyl)-oxazol-2-yl]-pentanoic acid methyl ester

Product 1

HCID 684943605-[5-(5-Chloro-2-hydroxy-phenyl)-oxazol-2-yl]-pentanoic acidYield 60.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Dissolve 5-[5-(5-chloro-2-hydroxy-phenyl)-oxazol-2-yl]-pentanoic acid methyl ester (3.26 g, 10.52 mmol) in 50 mL of dioxane and add a solution of LiOH (1.2671 g, 50.91 mmol) in 25 mL of water to it. Allow the reaction to stir at ambient temperature for 18 hours. Acidify the reaction with 5N HCl and concentrate the reaction mixture in vacuo to remove the dioxane. Extract the aqueous residue with EtOAc (3×). Dry the combined organic layers with MgSO4. Filter off the drying agent and concentrate in vacuo to afford a crude residue. Triturate the residue in cold EtOAc. Collect the product via filtration to afford 1.8837 g of the titled product (60%): mass spectrum: m/z=296.1 (M+H).

Workup

  1. customthe reaction
  2. concentrationconcentrate the reaction mixture in vacuo
  3. customto remove the dioxane
  4. extractionExtract the aqueous residue with EtOAc (3×)
  5. dry with materialDry the combined organic layers with MgSO4
  6. filtrationFilter off the drying agent
  7. concentrationconcentrate in vacuo
  8. customto afford a crude residue
  9. customTriturate the residue in cold EtOAc
  10. customCollect the product
  11. filtrationvia filtration

Sources & evidence

ORD record
ord-cd112616fc6349659a26fe140b2bacce
Source dataset
uspto-grants-2013_10
Patent number
US08552039B2

Reaction notes

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