Hydrochloric Acid → 2-(2,3,4-Trifluoroanilino)propionic acid
Reaction equation
CC(C)([O-])C.[K+].[F:7][C:8]1[C:20]([F:21])=[C:19]([F:22])[CH:18]=[CH:17][C:9]=1[NH:10][C@H:11]([CH3:16])[C:12]([O:14]C)=[O:13].[OH-].[Na+].Cl>CC(N(C)C)=O>[F:7][C:8]1[C:20]([F:21])=[C:19]([F:22])[CH:18]=[CH:17][C:9]=1[NH:10][CH:11]([CH3:16])[C:12]([OH:14])=[O:13]Participants
Procedure
Potassium tertiary-butoxide (123.4 mg) was suspended in DMAc (2 ml). Under ice-cooling, a solution of methyl (2R)-2-(2,3,4-trifluoroanilino)propionate (223 mg, 91% ee) in DMAc (2 ml) was added thereto. The liquid reaction mixture was stirred at the same temperature for 1 hour. Then an aqueous solution of sodium hydroxide (3 mol/l; 2 ml) was added and the mixture was stirred for 1 hour. The liquid reaction mixture was adjusted to pH 2 with an aqueous solution of hydrochloric acid (3 mol/l) and then extracted with IPE. The organic layer was dried over anhydrous magnesium sulfate and evaporated. The crude product thus obtained was recrystallized from a solvent mixture of methylene chloride with normal hexane to thereby give the title compound (206 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
- temperatureUnder ice-cooling
- customThe liquid reaction mixture
- stirringthe mixture was stirred for 1 hour
- customThe liquid reaction mixture
- extractionextracted with IPE
- dry with materialThe organic layer was dried over anhydrous magnesium sulfate
- customevaporated
- customThe crude product thus obtained
- customwas recrystallized from a solvent mixture of methylene chloride with normal hexane
Sources & evidence
- ORD record
- ord-d8f5fe38878e4845aa9d2fccfd26c16b
- Source dataset
- uspto-grants-2007_03
- Patent number
- US07189847B2
Reaction notes
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