Triethylamine → N-(2-Naphthylsulfonyl)-D-phenylalanylproline (p-cyanobenzyl)amide

HRID 1459005Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1459005
Cl.[NH:2]1[CH2:9][CH2:8][CH2:7][C@H:3]1[C:4]([NH2:6])=[O:5].[CH:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][C:11]=1[S:20]([NH:23][C@@H:24]([C:32]([OH:34])=O)[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)(=[O:22])=[O:21].[CH2:35]([N:37](CC)CC)C.ON1[C:47]2[CH:48]=[CH:49][CH:50]=[CH:51][C:46]=2N=N1.[CH:52]1(N=C=NC2CCCCC2)CCCCC1>CN(C=O)C.C(OCC)(=O)C>[C:35]([C:46]1[CH:51]=[CH:50][C:49]([CH2:52][NH:6][C:4](=[O:5])[C@@H:3]2[CH2:7][CH2:8][CH2:9][N:2]2[C:32](=[O:34])[C@@H:24]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[NH:23][S:20]([C:11]2[CH:12]=[CH:13][C:14]3[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:10]=2)(=[O:22])=[O:21])=[CH:48][CH:47]=1)#[N:37]

Komponenten

8

Edukt 5

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 1115233N-(2-naphthylsulfonyl)-D-phenylalanineHCID 12707183(S)-Pyrrolidine-2-carboxamide monohydrochloride

Produkt 1

HCID 53690380N-(2-Naphthylsulfonyl)-D-phenylalanylproline (p-cyanobenzyl)amide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

5.9 g (21.3 mmol) of the above proline amide hydrochloride were dissolved in 100 ml of DMF and successively 7.8 g (21.3 mmol) of N-(2-naphthylsulfonyl)-D-phenylalanine (A. Bernat et al., FR 2593812), 2.15 g (21.3 mmol) of triethylamine and 3.25 g (21.3 mmol) 1-hydroxybenzotriazole (HOBT) were added. While stirring at 0°-5° C., a solution of 4.4 g (21.3 mmol) of dicyclohexylcarbodiimide in 30 ml of ethyl acetate was added, and the mixture was then stirred at room temperature for 48 h.

Aufarbeitung

  1. stirringthe mixture was then stirred at room temperature for 48 h.

Quellen und Nachweise

ORD-Eintrag
ord-3bce3a288e8842d3bc7f1aa04a32e82e
Quelldatensatz
uspto-grants-1998_12
Patentnummer
US05852051

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