Hydrochloric Acid → 2-Hydroxy-4-[4-[3-(5-methyl-2-phenyl-4-oxazolyl) propionyl)phenyl]butyric acid

HRID 977245Notes

Reaction equation

HRID 977245 reaction equation
C([O:4][CH:5]([CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16](=[O:31])[CH2:17][CH2:18][C:19]2[N:20]=[C:21]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[O:22][C:23]=2[CH3:24])=[CH:12][CH:11]=1)C#N)(=O)C.Cl.[O:33]1[CH2:38]COCC1.[OH2:39]>>[OH:4][CH:5]([CH2:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([C:16](=[O:31])[CH2:17][CH2:18][C:19]2[N:20]=[C:21]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[O:22][C:23]=2[CH3:24])=[CH:14][CH:15]=1)[C:38]([OH:33])=[O:39]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 312751,4-DioxaneHCID 199656432-Acetoxy-4-[4-[3-(5-methyl-2-phenyl-4-oxazolyl)propionyl]phenyl]butyronitrile

Product 1

HCID 199656142-Hydroxy-4-[4-[3-(5-methyl-2-phenyl-4-oxazolyl) propionyl)phenyl]butyric acid

Procedure

A mixture of 2-acetoxy-4-[4-[3-(5-methyl-2-phenyl-4-oxazolyl)propionyl]phenyl]butyronitrile (1.72 g), 6 N HCl (20 ml) and dioxane (10 ml) was heated under refluxing conditions for 3 hours. The reaction mixture was poured over water and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4) and then concentrated under reduced pressure to yield 2-hydroxy-4-[4-[3-(5-methyl-2-phenyl-4-oxazolyl) propionyl)phenyl]butyric acid as a solid substance. The solid was dissolved in ethanolic hydrogen chloride (10%, w/w, 20 ml), followed by stirring at 75°-80° C. for 2 hours. The reaction mixture was poured over water and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4) and then concentrated under reduced pressure; the residue was subjected to silica gel column chromatography. From the fraction eluted with ethyl acetate-hexane (1:1), 2-hydroxy-4-[4-[3-(5-methyl-2-phenyl4-oxazolyl)propionyl]phenyl]butyric acid ethyl ester (1.54 g, 88%) was obtained, which was then recrystallized from dichloromethane-isopropyl ether to yield colorless needles having a melting point of 87°-88° C.

Workup

  1. temperaturewas heated under refluxing conditions for 3 hours
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with water
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2c967835b7504568a80ed74758c5e913
Source dataset
uspto-grants-1997_03
Patent number
US05614544

Reaction notes

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