Hydrochloric Acid → 9-[4-(Diethoxyphosphorylmethoxy)-1-hydroxybut-2-oxy]guanine

HRID 345087Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 345087
C(OC([N:8](C(OC(C)(C)C)=O)[C:9]1[N:17]=[C:16]2[C:12]([N:13]=[CH:14][N:15]2[O:18][CH:19]([CH2:29][CH2:30][O:31][CH2:32][P:33]([O:38][CH2:39][CH3:40])([O:35][CH2:36][CH3:37])=[O:34])[CH2:20][O:21][Si](C(C)(C)C)(C)C)=[C:11]([O:41]C)[N:10]=1)=O)(C)(C)C.Cl>C(O)C>[CH2:36]([O:35][P:33]([CH2:32][O:31][CH2:30][CH2:29][CH:19]([O:18][N:15]1[CH:14]=[N:13][C:12]2[C:11](=[O:41])[NH:10][C:9]([NH2:8])=[N:17][C:16]1=2)[CH2:20][OH:21])([O:38][CH2:39][CH3:40])=[O:34])[CH3:37]

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 199935582-[Bis(t-butoxycarbonyl)amino]-9-[1-(t-butyldimethylsilyloxy)-4-(diethoxyphosphorylmethoxy)but-2-oxy]-6-methoxypurine

Produkt 1

HCID 1363411999-[4-(Diethoxyphosphorylmethoxy)-1-hydroxybut-2-oxy]guanineAusbeute 48 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of 2-[bis(t-butoxycarbonyl)amino]-9-[1-(t-butyldimethylsilyloxy)-4-(diethoxyphosphorylmethoxy)but-2-oxy]-6-methoxypurine (415 mg, 0.57 mmol) was dissolved in ethanol (5 ml) and 5M hydrochloric acid (0.6 ml) and heated under reflux for 3.5 h. The reaction was evaporated in vacuo and the residue chromatographed on silica, eluting with chloroform-methanol 10:1, affording 9-[4-(diethoxyphosphorylmethoxy)-1-hydroxybut-2-oxy]guanine (110 mg, 48%) as a pale tan solid. νmax (KBr) 3400, 1680, 1640 and 1600 cm-1 ; δH [(CD3)2SO] 1.22 (6H, t, J7.1 Hz, 2×CH2CH3), 1.91 (2H, m, CHCH2CH2O), 3.54 (2H, m, CH2OH), 3.74 (2H, m, CH2OCH2P), 3.85 (2H, d, J8.2 Hz, CH2P), 4.03 (4H, m, 2×CH2CH3), 4.30 (1H, m, HOCH2CH), 5.01 (1H, m, D2O exchangeable OH), 6.65 (2H, br.s, D2O exchangeable, NH2); m/z (FAB+ve Ion), 428 (MNa+), 406 (MH+).

Aufarbeitung

  1. temperatureunder reflux for 3.5 h
  2. customThe reaction was evaporated in vacuo
  3. customthe residue chromatographed on silica
  4. washeluting with chloroform-methanol 10:1

Quellen und Nachweise

ORD-Eintrag
ord-029d4490a18246e8a7885b05333a6b31
Quelldatensatz
uspto-grants-1991_10
Patentnummer
US05055458

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