Hydrochloric Acid → HCID 54312120, compound

HRID 583399Notes

Reaction equation

HRID 583399 reaction equation
C([O:3][C:4](=[O:34])[CH2:5][CH2:6][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)[CH2:6][CH2:5][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 86754320HCID 86754320, compound

Product 1

HCID 54312120HCID 54312120, compound

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

A solution of 25 g of 4-[N'-methyl-N'-(3,5-bistrifluoromethyl-benzoyl)-amino]-5-(4-chloro-phenyl)-pentanoic acid ethyl ester and 18 g of lithium hydroxide monohydrate in 120 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 residue is recrystallised from diethyl ether/petroleum ether. In this way the title compound is obtained in the form of white crystals (m.p. 125-127°).

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
  5. customThe residue is recrystallised from diethyl ether/petroleum ether

Sources & evidence

ORD record
ord-b323836498e04eca8459e64ca02cce4a
Source dataset
uspto-grants-1999_07
Patent number
US05929067

Reaction notes

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