HCID 86608357, Verbindung → N-(3-Sulfopropyl)-L-phenylalanine

HRID 239774Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 239774
C([O:3][C:4](=[O:21])[C@H:5]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[NH:6][CH2:7][CH2:8][CH2:9][S:10]([OH:13])(=[O:12])=[O:11])C>[OH-].[Na+]>[C:15]1([CH2:14][C@H:5]([NH:6][CH2:7][CH2:8][CH2:9][S:10]([OH:13])(=[O:11])=[O:12])[C:4]([OH:21])=[O:3])[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Komponenten

3

Edukt 1

HCID 86608357HCID 86608357, Verbindung

Produkt 1

HCID 16036063N-(3-Sulfopropyl)-L-phenylalanineAusbeute 84,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

The N-(3-sulfo-propyl)-phenylalanine ethyl ester (DM-258-069, 860 mg, 2.7 mmol) was dissolved in 2N NaOH (1.2 g of NaOH and 15 mL of water). The reaction was stirred at room temperature overnight. Dowex Marathon C ion exchange resin (strongly acidic) was added to the solution. The suspension was stirred for 15 minutes before the resin was removed by filtration. The filtrate was evaporated under reduced pressure and lyophilized, affording the title compound (654 mg, 84%). 1H NMR (D2O, 500 MHz) δ ppm 7.20 (m, 5H), 3.96 (t, 1H, J=6.3 Hz), 3.11 (m, 4H), 2.80 (t, 2H, J=7.3 Hz), 1.95 (m, 2H). 13C (D2O, 125 MHz) δ ppm 171.46, 134.03, 129.50, 129.28, 128.10, 62.02, 47.97, 45.64, 35.23, 21.39. [α]D=+14.9° (c=0.0013 in water), ES-MS 286 (M−1).

Aufarbeitung

  1. additionDowex Marathon C ion exchange resin (strongly acidic) was added to the solution
  2. stirringThe suspension was stirred for 15 minutes before the resin
  3. customwas removed by filtration
  4. customThe filtrate was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-5e9c469b201f49d184212e5f19920cd2
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642801B2

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