Triethylamine → benzyl (3R)-4-(5-cyano-2-iodophenoxy)-3-(4-dimethylcarbamoylbenzoylamino)butyrate

HRID 747770Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 747770
[Cl-].[CH2:2]([O:9][C:10]([CH2:12][C@@H:13]([NH3+:25])[CH2:14][O:15][C:16]1[CH:21]=[C:20]([C:22]#[N:23])[CH:19]=[CH:18][C:17]=1[I:24])=[O:11])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:26][N:27]([CH3:39])[C:28]([C:30]1[CH:38]=[CH:37][C:33]([C:34](O)=[O:35])=[CH:32][CH:31]=1)=[O:29].ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C.Cl.CN(C)CCCN=C=NCC>ClCCl.O>[C:22]([C:20]1[CH:19]=[CH:18][C:17]([I:24])=[C:16]([CH:21]=1)[O:15][CH2:14][C@H:13]([NH:25][C:34](=[O:35])[C:33]1[CH:32]=[CH:31][C:30]([C:28](=[O:29])[N:27]([CH3:39])[CH3:26])=[CH:38][CH:37]=1)[CH2:12][C:10]([O:9][CH2:2][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1)=[O:11])#[N:23]

Komponenten

8

Edukt 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 110954804-(Dimethylcarbamoyl)benzoic acidHCID 86760714(1R)-1-benzyloxycarbonylmethyl-2-(5-cyano-2-iodophenoxy)ethylammonium chloride

Produkt 1

HCID 54212177benzyl (3R)-4-(5-cyano-2-iodophenoxy)-3-(4-dimethylcarbamoylbenzoylamino)butyrate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

2.05 g (4.33 mmol) of (1R)-1-benzyloxycarbonylmethyl-2-(5-cyano-2-iodophenoxy)ethyl ammonium chloride, 1.25 g (6.49 mmol) of 4-dimethylcarbamoylbenzoic acid, 994 mg (7.35 mmol) of 1-hydroxybenzotriazole, and 2.71 ml (19.46 mmol) of triethylamine were dissolved in 25 ml of dichloromethane, and 1.41 g (7.35 mmol) of 1-(3-dimethylaminopropyl)-3-ethyl carbodiimide hydrochloride was added thereto and stirred under cooling with ice for 10 minutes and then at room temperature for 18 hours. The reaction was stopped by adding water, and the title compound was obtained in an ordinary manner by treatment with dichloromethane as the extractant to obtain the crude product. It was purified by silica gel column chromatography (hexane:ethyl acetate=3:1, v/v) to obtain the title compound.

Aufarbeitung

  1. temperatureunder cooling with ice for 10 minutes

Quellen und Nachweise

ORD-Eintrag
ord-558a342599224a5d8e323c80e519f1b9
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07396844B1

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