1-Phenethylamine, (-)- → (S)-3-[2-(4-Fluoro-2-methyl-phenyl)-ethyl]-3-hydroxy-4-methyl-pentanoic Acid

HRID 1859528Notes

Reaction equation

HRID 1859528 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C@:10]([OH:18])([CH:15]([CH3:17])[CH3:16])[CH2:11][C:12]([OH:14])=[O:13])=[CH:4][CH:3]=1.[CH3:19][C@H](N)C1C=CC=CC=1>CCOC(C)=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][C@@:10]([OH:18])([CH:15]([CH3:16])[CH3:17])[CH2:11][C:12]([OH:14])=[O:13])=[C:6]([CH3:19])[CH:7]=1

Participants

4

Reactant 2

HCID 758181-Phenethylamine, (-)-HCID 53862325(R)-3-[2-(4-Fluoro-phenyl)-ethyl]-3-hydroxy-4-methyl-pentanoic Acid

Product 1

HCID 53925175(S)-3-[2-(4-Fluoro-2-methyl-phenyl)-ethyl]-3-hydroxy-4-methyl-pentanoic Acid

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Compound G-16 (enriched—62% (S)-enantiomer/38% (R) enantiomer) (11.1 g, 41.5 mmol) was dissolved in 120 mL EtOAc and treated with (S)-α-methylbenzylamine (6.52 g, 53.79 mmol). The resulting suspension was heated to reflux until all solids dissolved, at which time the solution was allowed to cool to room temperature overnight. The reaction flask was cooled to 0° C. for 1 hour. The resulting solids were filtered off and washed with cold Et2O. HPLC analysis of isolated solid (as the free acid): (AS chiralpak column, 0.8 mL/min., 98% Hexanes/2% IPA/+0.1% Formic acid).

Workup

  1. temperatureThe resulting suspension was heated
  2. temperatureto reflux until all solids
  3. dissolutiondissolved, at which time the solution
  4. temperatureThe reaction flask was cooled to 0° C. for 1 hour
  5. filtrationThe resulting solids were filtered off
  6. washwashed with cold Et2O

Sources & evidence

ORD record
ord-544b208ee4084ea2af7bcccb65855b48
Source dataset
uspto-grants-2003_03
Patent number
US06528510B1

Reaction notes

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