Triphenylphosphine → HCID 131723880, Verbindung

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Reaktionsgleichung

C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.P([O-])(OCC1C=CC=CC=1)(OCC1C=CC=CC=1)=O.[CH3:39][N:40]1[C:48]2[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=2)[C:42]([C:49]2[C:50](=[O:76])[N:51]([CH2:68][O:69][C:70](=[O:75])[NH:71]CCO)[C:52](=[O:67])[C:53]=2[C:54]2[C:62]3[C:57](=[CH:58][C:59]([N+:63]([O-:65])=[O:64])=[CH:60][CH:61]=3)[N:56]([CH3:66])[CH:55]=2)=[CH:41]1>C1COCC1>[CH3:39][N:40]1[C:48]2[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=2)[C:42]([C:49]2[C:50](=[O:76])[N:51]([CH2:68][O:69][C:70](=[O:75])[NH2:71])[C:52](=[O:67])[C:53]=2[C:54]2[C:62]3[C:57](=[CH:58][C:59]([N+:63]([O-:65])=[O:64])=[CH:60][CH:61]=3)[N:56]([CH3:66])[CH:55]=2)=[CH:41]1

Komponenten

Reaktionsbedingungen

Temperatur: -78 °C

Versuchsvorschrift

Triphenylphosphine (95 mg, 0.36 mmol) and dibenzyl phosphate (101 mg, 0.36 mmol) were added to a solution of (2-Hydoxy-ethyl)-carbamic acid 3-(1-methyl-1H-indol-3-yl)-4-(1-methyl-6-nitro-1H-indol-3-yl)-2,5-dioxo-2,5-dihydro-pyrrol-1-ylmethyl ester, prepared as in example 19 (150 mg, 0.289 mmol) in THF (6 mL). The mixture was cooled at −78° C. Diethyl azodicarboxiate (0.057 mL, 0.36 mmol) was added dropwise over 5 min. The cooling bath was removed and the mixture was stirred overnight. The mixture was then evaporated. Chromatography of the residue over silica gel using 2:1-4:1 EtOAc/hexanes gave [2-bis-benzyloxy-phosphoryloxy)-ethyl]-carbamic acid 3-(1-methyl-1H-indol-3-yl)-4-(1-methyl-6-nitro-1H-indol-3-yl)-2,5-dioxo-2,5-dihydro-pyrrol-1-ylmethyl ester (121 mg, 54%).

Aufarbeitung

additionDiethyl azodicarboxiate (0.057 mL, 0.36 mmol) was added dropwise over 5 min
customThe cooling bath was removed
customThe mixture was then evaporated

Quellen und Nachweise

ORD-Eintrag: ord-5920eaef75b444e2995e032250df7c23
Quelldatensatz: uspto-grants-2003_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06559164B1

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