Triphenylphosphine → 9-((1R,4S)-4-(Di-Boc-amino)-cyclopent-2-enyl)-6-((S)-1-hydroxymethyl-2-phenyl-ethylamino)-9H-purine-2-carboxylic acid methyl ester

HRID 215886Notizen

Reaktionsgleichung

[CH3:1][O:2][C:3]([C:5]1[N:13]=[C:12]2[C:8]([N:9]=[CH:10][N:11]2[C@@H:14]2[CH2:18][C@H:17](OC(OCC)=O)[CH:16]=[CH:15]2)=[C:7]([NH:25][C@H:26]([CH2:34][OH:35])[CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[N:6]=1)=[O:4].[NH:36]([C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])[C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:1][O:2][C:3]([C:5]1[N:13]=[C:12]2[C:8]([N:9]=[CH:10][N:11]2[C@@H:14]2[CH2:18][C@H:17]([N:36]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[C:44]([O:46][C:47]([CH3:48])([CH3:49])[CH3:50])=[O:45])[CH:16]=[CH:15]2)=[C:7]([NH:25][C@H:26]([CH2:34][OH:35])[CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[N:6]=1)=[O:4]

Komponenten

Reaktionsbedingungen

Temperatur: 50 °C

Versuchsvorschrift

9-((1R,4S)-4-Ethoxycarbonyloxy-cyclopent-2-enyl)-6-((S)-1-hydroxymethyl-2-phenyl-ethylamino)-9H-purine-2-carboxylic acid methyl ester (Intermediate WB) (1 eq.), di-tert-butyl iminodicarboxylate (1.1 eq.), triphenylphosphane (0.15 eq.) and TEA are dissolved in THF (deoxygenated & dry).) Tris(dibenzylideneacetone)dipalladium(0) (0.05 eq.) is added and the reaction mixture is stirred at 50° C. for 1 hour. The reaction mixture is removed in vacuo and the title compound is obtained by column chromatography.

Aufarbeitung

customThe reaction mixture is removed in vacuo

Quellen und Nachweise

ORD-Eintrag: ord-e4c5071b981644b2b7d254bb7e15138f
Quelldatensatz: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08193164B2

Notizen zur Reaktion

Wird geladen…