Hydrochloric Acid → HCID 54047873, compound

HRID 2289335Notes

Reaction equation

HRID 2289335 reaction equation
[F:1][C:2]([F:23])([F:22])[CH2:3][O:4][C:5]1[CH:10]=[C:9]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[CH:8]=[CH:7][C:6]=1[CH2:17][C:18]([O:20]C)=[O:19].O.O[Li].O.Cl>C1COCC1>[F:23][C:2]([F:1])([F:22])[CH2:3][O:4][C:5]1[CH:10]=[C:9]([N:11]2[CH2:12][CH2:13][O:14][CH2:15][CH2:16]2)[CH:8]=[CH:7][C:6]=1[CH2:17][C:18]([OH:20])=[O:19]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 54395758HCID 54395758, compound

Product 1

HCID 54047873HCID 54047873, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of methyl 2-(2,2,2-trifluoroethoxy)-4-(4-morpholinyl)phenylacetate (0.22 g, 0.67 mmol) from Step 2 above in THF (2 mL) and water (0.5 mL) was added LiOH.H2O (0.056 g, 1.3 mmol). The mixture was stirred at ambient temperature for 14 h. The solution was adjusted to pH 3 by the addition of 5 N aqueous HCl and the solvents were removed under reduced pressure and the residue was purified by pressurized silica gel column chromatography using a gradient elution of 0-50% MeOH:CH2Cl2 as eluant. 2-(2,2,2-Trifluoroethoxy)-4-(4-morpholinyl)phenylacetic acid was obtained as a gum (HPLC retention time=5.8 min (method A)).

Workup

  1. customthe solvents were removed under reduced pressure
  2. customthe residue was purified by pressurized silica gel column chromatography
  3. washa gradient elution of 0-50% MeOH

Sources & evidence

ORD record
ord-8c1871dec4dd471598088d09f3ec957d
Source dataset
uspto-grants-2000_07
Patent number
US06090805

Reaction notes

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