1-Phenethylamine, (+)- → HCID 131724810, compound

HRID 985663Notes

Reaction equation

HRID 985663 reaction equation
[F:1][C:2]1[C:13]([F:14])=[C:12]([F:15])[CH:11]=[CH:10][C:3]=1[NH:4][CH:5]([CH3:9])[C:6]([OH:8])=[O:7].[C:16]1([C@H:22]([NH2:24])[CH3:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CO>[C:16]1([C@H:22]([NH2:24])[CH3:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[F:1][C:2]1[C:13]([F:14])=[C:12]([F:15])[CH:11]=[CH:10][C:3]=1[NH:4][C@@H:5]([CH3:9])[C:6]([OH:8])=[O:7]

Participants

4

Reactant 2

HCID 6431891-Phenethylamine, (+)-HCID 220158662-(2,3,4-Trifluoroanilino)propionic acid

Product 1

HCID 131724810HCID 131724810, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

2-(2,3,4-Trifluoroanilino)propionic acid (1.1 g) was dissolved in a solvent mixture (15 ml; methanol-IPE=1:20). At room temperature, a solution (15 ml) of (R)-1-phenylethylamine (333.2 mg) in a solvent mixture (methanol-IPE=1:20) was slowly added thereto. The obtained suspension was stirred at room temperature for additional 2 hours and then filtered while washing with IPE. Thus, the title compound was obtained as colorless crystals (802 mg). The optical purity of this product was 80% ee. Subsequently, chloroform was added to the obtained salt and the mixture was stirred at 50° C. for 18 hours. Then the suspension was filtered while washing with IPE to give 703 mg of the title compound as colorless crystals. The optical purity of this product was 99% ee.

Workup

  1. filtrationfiltered
  2. washwhile washing with IPE

Sources & evidence

ORD record
ord-e7d033fd7a2648898a246c71cfee5143
Source dataset
uspto-grants-2005_03
Patent number
US06872823B1

Reaction notes

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