Benzyl chloroformate → benzyl N-(4-chloro-3-nitrophenyl)carbamate

HRID 1366111

Reaktionsgleichung

Reaktionsgleichung von HRID 1366111
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[C:12](Cl)([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13].C(N(C(C)C)CC)(C)C>ClCCl>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:12](=[O:13])[O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10]

Komponenten

5

Edukt 3

HCID 10387Benzyl chloroformateHCID 124774-Chloro-3-nitroanilineHCID 81531Diisopropylethylamine

Produkt 1

HCID 4935650benzyl N-(4-chloro-3-nitrophenyl)carbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

In one example, 4-chloro-3-nitroaniline reacted with CbzCl in dichloromethane in the presence of diisopropylethylamine. The product benzyl 4-chloro-3-nitrophenylcarbamate was isolated following flash chromatography. Following procedures in Examples 12, 13, and 15, final product benzyl 1-(2-acetamidoethyl)-3-(4-methoxyphenyl)-2-oxo-1,2-dihydroquinoxalin-6-ylcarbamate was isolated following reverse-phase HPLC with C(18) column eluting with water and acetonitrile. The product of the reaction, benzyl 1-(2-acetamidoethyl)-3-(4-methoxyphenyl)-2-oxo-1,2-dihydroquinoxalin-6-ylcarbamate, is a compound of formula I in which R1 is —CH2CH2NHAc, R2 is benzyloxycarbonyl, R3 is 4-methoxyphenyl.

Quellen und Nachweise

ORD-Eintrag
ord-1aa8b452bd6044edbec9610814f5d3e2
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07893066B2

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