Hydrochloric Acid → HCID 53723640, compound

HRID 583397Notes

Reaction equation

HRID 583397 reaction equation
C([O:3][C:4](=[O:34])[CH:5]=[CH:6][CH:7]([N:16]([CH3:33])[C:17](=[O:32])[C:18]1[CH:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:21]=[C:20]([C:28]([F:31])([F:30])[F:29])[CH:19]=1)[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=1)C.O.[OH-].[Li+].O.Cl>C1COCC1.CO.O>[CH3:33][N:16]([CH:7]([CH2:8][C:9]1[CH:10]=[CH:11][C:12]([Cl:15])=[CH:13][CH:14]=1)[CH:6]=[CH:5][C:4]([OH:34])=[O:3])[C:17](=[O:32])[C:18]1[CH:19]=[C:20]([C:28]([F:29])([F:30])[F:31])[CH:21]=[C:22]([C:24]([F:25])([F:26])[F:27])[CH:23]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 53721008HCID 53721008, compound

Product 1

HCID 53723640HCID 53723640, compound

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

A solution of 20 g of 4-[N'-methyl-N'-(3,5-bistrifluoromethyl-benzoyl)-amino]-5-(4-chlorophenyl)-pent-2-enoic acid ethyl ester and 15 g of lithium hydroxide monohydrate in 100 ml of THF/methanol/water 3:3:1 is stirred at room temperature for 4 hours, and then 200 ml of water and 1N hydrochloric acid are added (pH value approx. 2). The mixture is extracted twice with ethyl acetate. The combined organic phases are washed with water and saturated NaCl solution, dried (magnesium sulfate) and concentrated by evaporation. The title compound is obtained in the form of a colourless oil which can be used further without being further purified.

Workup

  1. extractionThe mixture is extracted twice with ethyl acetate
  2. washThe combined organic phases are washed with water and saturated NaCl solution
  3. dry with materialdried (magnesium sulfate)
  4. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-0b12db583f8b49c299b9c6b2cbe5d719
Source dataset
uspto-grants-1999_07
Patent number
US05929067

Reaction notes

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