Hydrochloric Acid → N-5984

HRID 2269672Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2269672
[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:8]([OH:29])[CH2:9][NH:10][C@H:11]([CH3:28])[CH2:12][C:13]2[CH:27]=[CH:26][C:16]3[O:17][C@@H:18]([C:21]([O:23]CC)=[O:22])[CH2:19][O:20][C:15]=3[CH:14]=2)[CH:5]=[CH:6][CH:7]=1.O.Cl>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:8]([OH:29])[CH2:9][NH:10][C@H:11]([CH3:28])[CH2:12][C:13]2[CH:27]=[CH:26][C:16]3[O:17][C@@H:18]([C:21]([OH:23])=[O:22])[CH2:19][O:20][C:15]=3[CH:14]=2)[CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 11200952HCID 11200952, Verbindung

Produkt 1

HCID 9865284N-5984Ausbeute 67,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of ethyl 6-(2-(R)-((2-(R)-(3-chlorophenyl)-2-hydroxyethyl)amino)propyl)-2,3-dihydro-1,4-benzodioxin-2-(R)-carboxylate (650 mg) in ethanol (2 ml) were added water (20 ml) and concentrated hydrochloric acid (0.32 ml). This solution was stirred under reflux-heating for 5 hours while removing ethanol with Dean-Stark apparatus. After the solution was concentrated under reduced pressure, acetonitrile/water (1/1) (11 ml) was added to the residue, which was then dissolved under heating. The solution was neutralized with a 5% aqueous solution of sodium hydrogencarbonate. Acetonitrile (20 ml) was added, and the crystals precipitated were dissolved under heating. The resulting solution was filtered under heating and then cooled, and the resulting crystals were filtered to give 6-(2-(R)-((2-(R)-(3-chlorophenyl)-2-hydroxyethyl)amino)-propyl)-2,3-dihydro-1,4-benzodioxin-2-(R)-carboxylic acid (412 mg). The HPLC-2 analysis of the optical isomer showed 96.5% purity (R/S=96.5/3.5, the purity of the material optical isomer used=90.5%).

Aufarbeitung

  1. temperatureunder reflux-heating for 5 hours
  2. customwhile removing ethanol with Dean-Stark apparatus
  3. concentrationAfter the solution was concentrated under reduced pressure, acetonitrile/water (1/1) (11 ml)
  4. additionwas added to the residue, which
  5. dissolutionwas then dissolved
  6. temperatureunder heating
  7. additionAcetonitrile (20 ml) was added
  8. customthe crystals precipitated
  9. dissolutionwere dissolved
  10. temperatureunder heating
  11. filtrationThe resulting solution was filtered
  12. temperatureunder heating
  13. temperaturecooled
  14. filtrationthe resulting crystals were filtered

Quellen und Nachweise

ORD-Eintrag
ord-f94f4aeab23745dc852a5f53ca4c4428
Quelldatensatz
uspto-grants-2001_12
Patentnummer
US06329533B2

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