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

HRID 1459005Notes

Reaction equation

HRID 1459005 reaction equation
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]

Participants

8

Reactant 5

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-3bce3a288e8842d3bc7f1aa04a32e82e
Source dataset
uspto-grants-1998_12
Patent number
US05852051

Reaction notes

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