Hydrochloric Acid → N-5984

HRID 325098Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 325098
[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-49aaa17927824d9a87b871c340f3e575
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06222050B1

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