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

HRID 345087Notes

Reaction equation

HRID 345087 reaction equation
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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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+).

Workup

  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

Sources & evidence

ORD record
ord-029d4490a18246e8a7885b05333a6b31
Source dataset
uspto-grants-1991_10
Patent number
US05055458

Reaction notes

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