Triphenylphosphine → Dibenzyl azodicarboxylate

HRID 1097652

Reaktionsgleichung

Reaktionsgleichung von HRID 1097652
[Cl:1][C:2]1[N:10](CC=C)[C:9]2[C:8](=[O:14])[NH:7][C:6](=[O:15])[N:5]([CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[C:4]=2[N:3]=1.[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][C:29]2[N:33]=[C:32]([CH2:34][CH2:35][CH2:36]O)[O:31][N:30]=2)=[CH:24][CH:23]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH:57]1[CH:62]=[CH:61][C:60]([CH2:63][O:64][C:65](/[N:67]=[N:68]/[C:69]([O:71][CH2:72][C:73]2[CH:78]=[CH:77][CH:76]=[CH:75][CH:74]=2)=[O:70])=[O:66])=[CH:59][CH:58]=1>C1COCC1>[Cl:1][C:2]1[NH:10][C:9]2[C:8](=[O:14])[N:7]([CH2:36][CH2:35][CH2:34][C:32]3[O:31][N:30]=[C:29]([CH2:28][C:25]4[CH:24]=[CH:23][C:22]([Cl:21])=[CH:27][CH:26]=4)[N:33]=3)[C:6](=[O:15])[N:5]([CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[C:4]=2[N:3]=1.[CH:76]1[CH:75]=[CH:74][C:73]([CH2:72][O:71][C:69](/[N:68]=[N:67]/[C:65]([O:64][CH2:63][C:60]2[CH:61]=[CH:62][CH:57]=[CH:58][CH:59]=2)=[O:66])=[O:70])=[CH:78][CH:77]=1

Komponenten

7

Edukt 4

HCID 11776TriphenylphosphineHCID 5387121Dibenzyl azodicarboxylateHCID 592995577-Allyl-8-chloro-3-pentyl-1H-purine-2,6(3H,7H)-dioneHCID 668129393-{3-[(4-Chlorophenyl)methyl]-1,2,4-oxadiazol-5-yl}-1-propanol

Produkt 2

HCID 5387121Dibenzyl azodicarboxylateAusbeute 177,5 %HCID 593955258-Chloro-1-(3-{3-[(4-chlorophenyl)methyl]-1,2,4-oxadiazol-5-yl}propyl)-3-pentyl-3,7-dihydro-1H-purine-2,6-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 8-chloro-3-pentyl-7-(2-propen-1-yl)-3,7-dihydro-1H-purine-2,6-dione (0.10 g, 0.34 mmol), 3-{3-[(4-chlorophenyl)methyl]-1,2,4-oxadiazol-5-yl}-1-propanol (0.086 g, 0.34 mmol) and triphenylphosphine (0.186 g, 0.69 mmol) in THF (5 ml) was added dibenzylazodicarboxylate (0.204 g, 0.68 mmol) and the solution stirred for 18 h. The solution was then concentrated and the residues chromatographed over silica (20 g, SPE) eluting with DCM initially then DCM/Et2O mixtures to yield the title compound contaminated with dibenzylazodicarboxylate by-products (0.18 g). Material used crude in deprotection step.

Aufarbeitung

  1. concentrationThe solution was then concentrated
  2. customthe residues chromatographed over silica (20 g, SPE)
  3. washeluting with DCM initially

Quellen und Nachweise

ORD-Eintrag
ord-981292021ff24f748c5004279100e538
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08143264B2

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