Hydrochloric Acid → (R)-3-Hydroxy-4-methyl-3-(2-phenyl-ethyl)-pentanoic Acid

HRID 23454

Reaktionsgleichung

Reaktionsgleichung von HRID 23454
[OH:1][C@:2]([CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([CH:7]([CH3:9])[CH3:8])[CH2:3][C:4]([OH:6])=[O:5].Cl.C[C@@H](N)C1C=CC=CC=1>>[OH:1][C@@:2]([CH2:10][CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)([CH:7]([CH3:8])[CH3:9])[CH2:3][C:4]([OH:6])=[O:5]

Komponenten

4

Edukt 3

HCID 313Hydrochloric AcidHCID 6431891-Phenethylamine, (+)-HCID 54476673(S)-3-Hydroxy-4-methyl-3-(2-phenyl-ethyl)-pentanoic Acid

Produkt 1

HCID 54476674(R)-3-Hydroxy-4-methyl-3-(2-phenyl-ethyl)-pentanoic Acid

Versuchsvorschrift

The mother liquor from the isolation of diastereomeric salt G-10 (S) was treated with 1N HCl and extracted with EtOAc. The organic phase was washed with brine, dried (MgSO4), filtered and concentrated to liberate the free β-hydroxy acid. HPLC analysis indicated the isolated material was 73% (R):27% (S). β-Hydroxy acid G-10 (1 equiv.) was dissolved in 600 mL EtOAc and treated with (R)-α-methylbenzylamine (0.74 equiv.). The resulting suspension was placed on a steam bath and heated to reflux. The solution was allowed to cool to room temperature slowly and then cooled to 0° C. in an ice bath. The resulting solids were filtered off and washed with cold EtOAc followed by Et2O to yield the title compound. The free acid was obtained by treating the salt with 1N HCl followed by extraction with EtOAc. The organic phased was washed with brine, dried (MgSO4), filtered and concentrated to afford the resolved β-hydroxy acid. HPLC analysis of isolated solid (as the free acid): (OD chiralpak column, 1 mL/min., 97.5% Hexanes:2.5% IPA:+0.1% Formic acid)

Aufarbeitung

  1. extractionextracted with EtOAc
  2. washThe organic phase was washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. dissolutionβ-Hydroxy acid G-10 (1 equiv.) was dissolved in 600 mL EtOAc
  7. customThe resulting suspension was placed on a steam bath
  8. temperatureheated to reflux
  9. temperaturecooled to 0° C. in an ice bath
  10. filtrationThe resulting solids were filtered off
  11. washwashed with cold EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-deee898fc80b4b58a21ebfd1a671caa7
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06852711B2

Verknüpfte Notizen

Wird geladen…