Hydrochloric Acid → 2-(2,3,4-Trifluoroanilino)propionic acid
Reaction equation
[F:1][C:2]1[C:14]([F:15])=[C:13]([F:16])[CH:12]=[CH:11][C:3]=1[NH:4][C@H:5]([CH3:10])[C:6]([O:8]C)=[O:7].C(=O)([O-])[O-].[K+].[K+].[OH-].[Na+].Cl>CC(N(C)C)=O>[F:1][C:2]1[C:14]([F:15])=[C:13]([F:16])[CH:12]=[CH:11][C:3]=1[NH:4][CH:5]([CH3:10])[C:6]([OH:8])=[O:7]Participants
Conditions
- Temperature
- 95 °C
Procedure
Methyl (2R)-2-(2,3,4-trifluoroanilino)propionate (223 mg, 91% ee) was dissolved in DMAc (3 ml) and potassium carbonate (474.1 mg) was added thereto at room temperature. The liquid reaction mixture was stirred at 95° C. for 19 hours. After adding an aqueous solution of sodium hydroxide (3 mol/l), the liquid reaction mixture was stirred for 1 hour and then adjusted to pH 2 with hydrochloric acid (3 mol/l) followed by extraction with IPE. Next, it was dried over anhydrous magnesium sulfate. After evaporating the solvent, the crude product thus obtained was recrystallized from a solvent mixture of methylene chloride with normal hexane to thereby give the title compound (198 mg) as colorless crystals. The optical purity of this product was 0% ee. Various spectral data of this product was identical with those obtained in Example 23.
Workup
- customat room temperature
- customThe liquid reaction mixture
- customthe liquid reaction mixture
- stirringwas stirred for 1 hour
- extractionfollowed by extraction with IPE
- dry with materialNext, it was dried over anhydrous magnesium sulfate
- customAfter evaporating the solvent
- customthe crude product thus obtained
- customwas recrystallized from a solvent mixture of methylene chloride with normal hexane
Sources & evidence
- ORD record
- ord-0d94bae62b134576aecf16ab2364ced8
- Source dataset
- uspto-grants-2006_08
- Patent number
- US07087778B2
Reaction notes
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