Oxalyl chloride → Epoxysuccinic acid monoallylester chloride

HRID 1074636

Reaktionsgleichung

Reaktionsgleichung von HRID 1074636
[O:1]1[CH:6]([C:7]([OH:9])=[O:8])[CH:2]1[C:3]([OH:5])=[O:4].[CH2:10]([K])[CH:11]=[CH2:12].C(Cl)(=O)C([Cl:17])=O.C(OC(=O)[C@H](CC1C=CC(O)=CC=1)N)C1C=CC=CC=1>ClCCl>[Cl-:17].[CH2:12]([O:8][C:7](=[O:9])[CH:6]1[O:1][CH:2]1[C:3]([OH:5])=[O:4])[CH:11]=[CH2:10]

Komponenten

5

Edukt 3

HCID 65578Oxalyl chlorideHCID 104541(S)-Benzyl 2-amino-3-(4-hydroxyphenyl)propanoateHCID 178455845HCID 178455845, Verbindung

Produkt 1

HCID 86738951Epoxysuccinic acid monoallylester chloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

When 0.65 g of epoxysuccinic acid monoallylester chloride which was prepared from 1.0 g of allyl potassium epoxysuccinate (i.e. allyl potassium oxirane 2,3-dicarboxylate) by treatment with oxalyl chloride in a manner as described in Example 46 was reacted with L-tyrosine benzyl ester in dichloromethane by the method as described in Example 46, N-(3-allyloxycarbonyloxirane-2-carbonyl)-L-tyrosine benzyl ester(EP-147) was obtained as a colorless oil. Yield 1.0 g (68%). Mass: m/e 425 (M+). IRνfilm (cm-1): 3480 (amine, hydroxy), 1755 (ester), 1685, 1525 (amide), 1625 (C=C), 895 (epoxide). NMR(CDCl3)δ: 2.98 (2H, d, J=6 Hz), 3.19 (0.5H, d, J=2 Hz), 3.43 (0.5H, d, J=2 Hz), 3.58 (0.5H, d, J=2 Hz), 3.61 (0.5H, d, J=2 Hz), 4.5-6.2 (6H, m), 5.08 (2H, d, J=3 Hz), 6.25-7.0 (4H, m), 7.25 (5H, s).

Quellen und Nachweise

ORD-Eintrag
ord-c503354c8a8f4950bf70025239ec3486
Quelldatensatz
uspto-grants-1983_07
Patentnummer
US04393228

Verknüpfte Notizen

Wird geladen…