(S)-1-Phenyl-3-propanolamine → HCID 178431680, Verbindung

HRID 339881

Reaktionsgleichung

Reaktionsgleichung von HRID 339881
[NH2:1][C@H:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH2:3][CH2:4][OH:5].[Br:12][C:13]1[CH:14]=[C:15]([C:19]2([F:32])[C:24]([CH3:26])([CH3:25])[O:23][C:22](OCC)=[N:21][S:20]2(=[O:31])=[O:30])[CH:16]=[CH:17][CH:18]=1>ClCCl>[Br:12][C:13]1[CH:14]=[C:15]([C:19]2([F:32])[C:24]([CH3:25])([CH3:26])[O:23][C:22]([NH:1][C@H:2]([C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH2:3][CH2:4][OH:5])=[N:21][S:20]2(=[O:31])=[O:30])[CH:16]=[CH:17][CH:18]=1

Komponenten

4

Edukt 2

HCID 2734520(S)-1-Phenyl-3-propanolamineHCID 683592075-(3-Bromophenyl)-2-ethoxy-5-fluoro-6,6-dimethyl-5,6-dihydro-1,4,3-oxathiazine 4,4-dioxide

Produkt 1

HCID 178431680HCID 178431680, VerbindungAusbeute 24,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

In a round-bottom flask, 42 mg of 5-(3-bromophenyl)-2-ethoxy-5-fluoro-6,6-dimethyl-5,6-dihydro-1,4,3-oxathiazine 4,4-dioxide was dissolved under inert gas in 0.2 ml of dichloromethane and admixed with 20 mg of (S)-3-amino-3-phenylpropan-1-ol. After stirring at room temperature for 18 hours, the conversion was checked by LCMS. Since only traces of the product had formed, the reaction mixture was stirred at 100° C. for a further 4.5 hours. After the removal of the solvent under reduced pressure, the crude product was purified in a purification laboratory by means of preparative HPLC. The product-containing fractions were combined, the acetonitrile was removed under reduced pressure, and the aqueous residue was basified with saturated aqueous sodium hydrogencarbonate solution and extracted with ethyl acetate. The organic phase was dried over MgSO4 and concentrated by rotary evaporation, and the residue was taken up again in a mixture of acetonitrile and water and lyophilized. This gave the product (13.1 mg) with a molecular weight of 485.4 g/mol (C20H22BrFN2O4S); MS (ESI): m/e=485 (M+H+).

Aufarbeitung

  1. customSince only traces of the product had formed
  2. stirringthe reaction mixture was stirred at 100° C. for a further 4.5 hours
  3. customAfter the removal of the solvent under reduced pressure
  4. customthe crude product was purified in a purification laboratory by means of preparative HPLC
  5. customthe acetonitrile was removed under reduced pressure
  6. extractionextracted with ethyl acetate
  7. dry with materialThe organic phase was dried over MgSO4
  8. concentrationconcentrated by rotary evaporation
  9. additionthe residue was taken up again in a mixture of acetonitrile and water

Quellen und Nachweise

ORD-Eintrag
ord-aeeab59a5351419c86fe8f6bc64b2a5b
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08895547B2

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