Methanol → HCID 59775598, Verbindung

HRID 557465Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 557465
[NH2:1][CH:2]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([I:13])[CH:8]=1)[CH2:3][C:4]([OH:6])=[O:5].S(Cl)(Cl)=O.[CH3:18]O>>[CH3:18][O:5][C:4](=[O:6])[CH2:3][CH:2]([NH2:1])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([I:13])[CH:8]=1

Komponenten

4

Edukt 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 27723423-Amino-3-(3-iodophenyl)propanoic acid

Produkt 1

HCID 59775598HCID 59775598, VerbindungAusbeute 95 %

Versuchsvorschrift

To a suspension of (±)-3-Amino-3-(3-iodo-phenyl)-propionic acid (3.1 g, 10.6 mmol) in methanol was added thionyl chloride (0.95 mL, 12.7 mmol) and the reaction was stirred at room temperature overnight. Concentration followed by trituration with ether gives a white solid. The solid is filtered, washed with ether and dried to afford the desired product (3.5 g, 10 mmol, 95%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 8.79 (br, 2H), 8.01 (s, 1H), 7.74 (d, J=8.1 Hz, 1H). 7.57 (d, J=7.8 Hz, 1H), 7.21 (dd, J=8.1, 7.8 Hz, 1H), 4.56 (br, 1H), 3.54 (s, 3H), 3.23-3.17 (m, 1H), 3.04-2.98 (m, 1H).

Aufarbeitung

  1. concentrationConcentration
  2. customgives a white solid
  3. filtrationThe solid is filtered
  4. washwashed with ether
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-ac3dc423ba244e298f2c0f526680be5a
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08058449B2

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