Diisopropylethylamine → N-((1S,2R,3S,4R)-4-{6-[2,2-Bis-(4-hydroxy-phenyl)-ethylamino]-2-chloro-purin-9-yl}-2,3-dihydroxy-cyclopentyl)-propionamide hydrochloride

HRID 1882567

Reaktionsgleichung

Reaktionsgleichung von HRID 1882567
C(OC(=O)[N:7]([C@H:12]1[CH2:16][C@@H:15]([N:17]2[CH:25]=[N:24][C:23]3[C:18]2=[N:19][C:20]([Cl:27])=[N:21][C:22]=3[Cl:26])[C@H:14]([OH:28])[C@@H:13]1[OH:29])[C:8](=[O:11])[CH2:9][CH3:10])(C)(C)C.[NH2:31][CH2:32][CH:33]([C:41]1[CH:46]=[CH:45][C:44]([OH:47])=[CH:43][CH:42]=1)[C:34]1[CH:39]=[CH:38][C:37]([OH:40])=[CH:36][CH:35]=1.CCN(C(C)C)C(C)C>C1COCC1>[ClH:26].[OH:40][C:37]1[CH:38]=[CH:39][C:34]([CH:33]([C:41]2[CH:42]=[CH:43][C:44]([OH:47])=[CH:45][CH:46]=2)[CH2:32][NH:31][C:22]2[N:21]=[C:20]([Cl:27])[N:19]=[C:18]3[C:23]=2[N:24]=[CH:25][N:17]3[C@@H:15]2[CH2:16][C@H:12]([NH:7][C:8](=[O:11])[CH2:9][CH3:10])[C@@H:13]([OH:29])[C@H:14]2[OH:28])=[CH:35][CH:36]=1

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 217102804,4'-(2-Aminoethylidene)bisphenolHCID 44140426[(1S,2R,3S,4R)-4-(2,6-dichloro-purin-9-yl)-2,3-dihydroxy-cyclopentyl]-propionyl-carbamic acid tert-butyl ester2×

Produkt 1

HCID 86647554N-((1S,2R,3S,4R)-4-{6-[2,2-Bis-(4-hydroxy-phenyl)-ethylamino]-2-chloro-purin-9-yl}-2,3-dihydroxy-cyclopentyl)-propionamide hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A reaction mixture comprising [(1S,2R,3S,4R)-4-(2,6-dichloro-purin-9-yl)-2,3-dihydroxy-cyclopentyl]-propionyl-carbamic acid tert-butyl ester (Intermediate G) (2.00 g, 4.35 mmol) and 4,4′-(2-aminoethylidene)bis-phenol (prepared by the procedure of R. M. Schelkun et al. Bioorg. Med. Chem. Lett. 9 (1999) 2447-2452.) (1.19 g, 5.20 mmol) in dry THF (40 ml) is treated with DIPEA (0.67 g, 5.20 mmol) and stirred at room temperature for 2 days. The solvent is removed in vacuo and the title compound is obtained after purification by reverse phase column chromatography (Isolute™ C18, 20-70% acetonitrile in water −0.1% HCl).

Aufarbeitung

  1. customThe solvent is removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-6815395856ce45d1b40869e3937b17cf
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08318750B2

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