Reaktion #353541

ord-c38497fb5a514ea39d8aa4147fbfa9d2

Reaktionsgleichung

CCN(CC)CC
triethylamine
C[n+]1ccccc1Cl.[I-]
1-methyl-2-chloropyridinium iodide
CCCC(NS(=O)(=O)c1ccc(Cl)cc1)C(=O)O
(RS)-2-(4-chlorobenzenesulfonylamino)pentanoic acid
CCOC(=O)Cc1ccc(N)cc1.Cl
ethyl 4-aminophenylacetate hydrochloride
→
CCCC(NS(=O)(=O)c1ccc(Cl)cc1)C(=O)Nc1ccc(CC(=O)OCC)cc1
(RS)-2-(4-chlorobenzenesulfonylamino)-N-(4-(ethoxycarbonylmethyl)phenyl)pentanamide
Ausbeute 27.7%

Edukte

CCN(CC)CC
triethylamine
C[n+]1ccccc1Cl.[I-]
1-methyl-2-chloropyridinium iodide
CCCC(NS(=O)(=O)c1ccc(Cl)cc1)C(=O)O
(RS)-2-(4-chlorobenzenesulfonylamino)pentanoic acid
CCOC(=O)Cc1ccc(N)cc1.Cl
ethyl 4-aminophenylacetate hydrochloride

Reagenzien

Keine

Lösungsmittel

ClC(Cl)Cl
chloroform

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

The procedure described in Example 177 was repeated, except that (RS)-2-(4-chlorobenzenesulfonylamino)pentanoic acid (1 g) and ethyl 4-aminophenylacetate hydrochloride (665 mg) were condensed in chloroform (30 ml) in the presence of triethylamine (1.9 ml) and 1-methyl-2-chloropyridinium iodide (1.05 g) to obtain (RS)-2-(4-chlorobenzenesulfonylamino)-N-(4-(ethoxycarbonylmethyl)phenyl)pentanamide (387 mg).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05650428uspto-grants-1997_07