Hydrochloric Acid → 3-{4-(4-chlorophenyl)-2-[2-(methylsulfonyl)-1H-imidazol-1-yl]-5-oxazolyl}propionic acid

HRID 350732Notes

Reaction equation

HRID 350732 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([N:19]3[CH:23]=[CH:22][N:21]=[C:20]3[S:24]([CH3:27])(=[O:26])=[O:25])[O:11][C:12]=2[CH2:13][CH2:14][C:15]([O:17]C)=[O:16])=[CH:4][CH:3]=1.[OH-].[Na+].Cl>O1CCOCC1.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[C:10]([N:19]3[CH:23]=[CH:22][N:21]=[C:20]3[S:24]([CH3:27])(=[O:26])=[O:25])[O:11][C:12]=2[CH2:13][CH2:14][C:15]([OH:17])=[O:16])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21088779methyl 3-{4-(4-chlorophenyl)-2-[2-(methylsulfonyl)-1H-imidazol-1-yl]-5-oxazolyl}propionate

Product 1

HCID 230617453-{4-(4-chlorophenyl)-2-[2-(methylsulfonyl)-1H-imidazol-1-yl]-5-oxazolyl}propionic acidYield 90.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of methyl 3-{4-(4-chlorophenyl)-2-[2-(methylsulfonyl)-1H-imidazol-1-yl]-5-oxazolyl}propionate (1.4 g) in 1,4-dioxane (7 mL) was added 2N aqueous sodium hydroxide solution (3.5 mL) and the mixture was stirred at room temperature for 30 min. The reaction mixture was diluted with water, and acidified with 2N aqueous hydrochloric acid solution. The precipitated crystals were collected by filtration and recrystallized from methanol to give 3-{4-(4-chlorophenyl)-2-[2-(methylsulfonyl)-1H-imidazol-1-yl]-5-oxazolyl}propionic acid (1.22 g, yield 90%) as colorless prism crystals. melting point: 166–167° C.

Workup

  1. filtrationThe precipitated crystals were collected by filtration
  2. customrecrystallized from methanol

Sources & evidence

ORD record
ord-711ef09e49634c6fa34eb6f43fff85e9
Source dataset
uspto-grants-2007_02
Patent number
US07183276B2

Reaction notes

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