Triphenylphosphine → HCID 10255381, Verbindung

HRID 1708089

Reaktionsgleichung

Reaktionsgleichung von HRID 1708089
[OH:1][N:2]1[CH:10]=[N:9][C:8]2[C:3]1=[N:4][CH:5]=[N:6][C:7]=2[N:11]1[C:15](=[O:16])[C:14]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:13]2[C:12]1=[O:21].O[CH2:23][CH2:24]/[CH:25]=[CH:26]/[P:27](=[O:36])([O:32][CH:33]([CH3:35])[CH3:34])[O:28][CH:29]([CH3:31])[CH3:30].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[CH:33]([O:32][P:27](/[CH:26]=[CH:25]/[CH2:24][CH2:23][O:1][N:2]1[CH:10]=[N:9][C:8]2[C:3]1=[N:4][CH:5]=[N:6][C:7]=2[N:11]1[C:15](=[O:16])[C:14]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:13]2[C:12]1=[O:21])([O:28][CH:29]([CH3:30])[CH3:31])=[O:36])([CH3:35])[CH3:34]

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 10399205HCID 10399205, VerbindungHCID 145239709-Hydroxy-6-phthalimidopurine

Produkt 1

HCID 10255381HCID 10255381, VerbindungAusbeute 80,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a mixture of 9-hydroxy-6-phthalimidopurine (141 mg, 500 μmol), diisopropyl (E)-4-hydroxybut-1-enylphosphonate (110 g, 500 μmol) and triphenylphosphine (197 mg, 750 μmol) in tetrahydrofuran (5 ml) stirred at 0° C. was added diethyl azodicarboxylate (131 mg, 750 μmol). The mixture was then stirred at room temperature for 2 hr. The solvent was removed and the residue purified by column chromatography on silica gel eluting with dichloromethane-methanol (49:1, 16:1) to give (E)-9-[4-(diisopropoxyphosphoryl)but-3-enyloxy]-6-phthalimidopurine as a gum (200 mg, 80%); λmax (EtOH) 273 (14,380) nm; υmax (film) 2970, 1730 1590 1570 1355 1240 and 975 cm-1 ; δH [(CD3)2SO] 1.24 (12H, pseudo t, J 6 Hz, CH(CH3)2), 2.77 (2H, m, CH2), 4 60 (2H, m, CH(CH3)2), 4.66 (2H, t, J 6 Hz, CH2O ), 6.07 (1H, dd, J 17 Hz and 20 Hz, PCH=CH), 6.75 (1H, ddt, J 6 Hz, 17 Hz and 22 Hz, PCH=CH), 8.00-8.25 (4H, m, Ph), 9.00 (1H, s, H-2/H-8), 9.08 (1H, s, H-2/H-8) (Found: M+ 499. 1620. C23H26N5O6P requires M+ 499.1621).

Aufarbeitung

  1. stirringThe mixture was then stirred at room temperature for 2 hr
  2. customThe solvent was removed
  3. customthe residue purified by column chromatography on silica gel eluting with dichloromethane-methanol (49:1, 16:1)

Quellen und Nachweise

ORD-Eintrag
ord-c8fc4f318b8f4baeb437446062b6ae15
Quelldatensatz
uspto-grants-1994_10
Patentnummer
US05356886

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