Propane sultone → HCID 58931799, Verbindung

HRID 239780

Reaktionsgleichung

Reaktionsgleichung von HRID 239780
[NH2:1][C@@H:2]([C:10]([NH2:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH2:13]1[CH2:19][S:16](=[O:18])(=[O:17])[O:15][CH2:14]1>C(#N)C>[C:10]([C@H:2]([NH:1][CH2:14][CH2:13][CH2:19][S:16]([OH:18])(=[O:17])=[O:15])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=[O:11])[NH2:12]

Komponenten

4

Edukt 2

HCID 14264Propane sultoneHCID 7000171(2R)-2-amino-3-phenylpropanamide

Produkt 1

HCID 58931799HCID 58931799, VerbindungAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a solution of D-Phenylalaninamide (1.83 g, 11.1 mmol) in acetonitrile (20 mL) was added 1,3-propane sultone (1.29 g, 10.6 mmol). The solution was stirred at reflux for 2.5 hours. The reaction mixture was cooled to room temperature. The solid was filtered and washed with acetonitrile (2×20 mL). The solid product was suspended in EtOH (75 mL). The suspension was stirred at reflux for 1 hours. The solid material was filtered, washed with acetone (1×25 mL) and dried in vacuo, affording the title compound (2.62 g, 89%). 1H NMR (D2O, 500 MHz) δ ppm 7.28 (m, 3H), 7.19 (m, 2H), 4.05 (m, 1H), 3.19 (dd, 1H, J=5.3 Hz, 14.2 Hz), 3.04 (m, 3H), 2.86 (t, 2H, J=5.8 Hz), 2.03 (m, 2H). 13C (D2O, 125 MHz) δ ppm 170.39, 133.73, 129.62, 129.26, 128.15, 61.57, 47.99, 45.57, 36.21, 21.45. [α]D=−20.7° (c=0.0038 in water), ES-MS 285 (M−1).

Aufarbeitung

  1. temperatureat reflux for 2.5 hours
  2. filtrationThe solid was filtered
  3. washwashed with acetonitrile (2×20 mL)
  4. stirringThe suspension was stirred
  5. temperatureat reflux for 1 hours
  6. filtrationThe solid material was filtered
  7. washwashed with acetone (1×25 mL)
  8. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-1459b54d87904f3f8a56cb1f8a285f68
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642801B2

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