Diphosgene → Methyl 2-isocyanato-3-phenylpropanoate

HRID 248316

Reaktionsgleichung

Reaktionsgleichung von HRID 248316
Cl.[CH3:2][O:3][C:4](=[O:14])[C@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[NH2:6].Cl[C:16]([O:19]C(Cl)=O)(Cl)Cl>O1CCOCC1>[CH3:2][O:3][C:4](=[O:14])[CH:5]([N:6]=[C:16]=[O:19])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Komponenten

4

Edukt 2

HCID 10426DiphosgeneHCID 75736Methyl L-phenylalaninate hydrochloride

Produkt 1

HCID 2769481Methyl 2-isocyanato-3-phenylpropanoateAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

L-Phenylalanine methyl ester hydrochloride (6.00 g., 27.82 mmole) was slurried in anhydrous 1,4-dioxane (125 ml.), treated with trichloromethylchloroformate (5.05 ml., 41.86 mmole) and heated at 55° C. for 17.5 hours. The excess trichloromethylchloroformate and 1,4-dioxane were removed from the reaction mixture by distillation under slightly reduced pressure. The resultant residue was subjected to high vacuum distillation to afford the desired intermediate 2-isocyanato-3-phenylpropionic acid methyl ester (4.78 g., 84% yield). B.P. 83°-85° C. (100 μm Hg.) as a clear colorless liquid. 1H-NMR (200 MHz, CDCl3) δppm =3.12, dd, J=8.5 Hz., 2H (--CH2 --Ph), 3.83, s, 3H (--COOCH3), 4.28, m, 1H (--CH--CH2 --), 7.15-7.4, m, 5H (Ar--H).

Aufarbeitung

  1. customThe excess trichloromethylchloroformate and 1,4-dioxane were removed from the reaction mixture by distillation under slightly reduced pressure
  2. distillationThe resultant residue was subjected to high vacuum distillation

Quellen und Nachweise

ORD-Eintrag
ord-264a12d11093412292df397b1effc9b2
Quelldatensatz
uspto-grants-1993_05
Patentnummer
US05209930

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