HCID 53665397, compound → HCID 19993522, compound

HRID 345080Notes

Reaction equation

HRID 345080 reaction equation
[Si]([O:8][CH2:9][CH:10]([O:22][N:23]1[CH:31]=[N:30][C:29]2[C:24]1=[N:25][CH:26]=[N:27][C:28]=2[NH2:32])[CH2:11][O:12][CH2:13][P:14]([O:19][CH2:20][CH3:21])([O:16][CH2:17][CH3:18])=[O:15])(C(C)(C)C)(C)C>C(O)(=O)C>[CH2:17]([O:16][P:14]([CH2:13][O:12][CH2:11][CH:10]([O:22][N:23]1[CH:31]=[N:30][C:29]2[C:24]1=[N:25][CH:26]=[N:27][C:28]=2[NH2:32])[CH2:9][OH:8])([O:19][CH2:20][CH3:21])=[O:15])[CH3:18]

Participants

3

Reactant 1

HCID 53665397HCID 53665397, compound

Product 1

HCID 19993522HCID 19993522, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 9-(1-t-butyldimethylsilyloxy-3-diethoxyphosphorylmethoxyprop-2-oxy)adenine (170 mg, 0.35 mmol) in 80% aqueous acetic acid (5 ml) was stirred at 85° C. for 5 hours. After evaporation, the residue was chromatographed on silica eluting with ethyl acetate-methanol 5:1 affording 9-(1-diethoxyphosphorylmethoxy3-hydroxyprop-2-oxy)adenine (120 mg, 92%) as a clear gum. νmax (film) 3340; 1700, 1600, 1330, 1290, 1240, 1030 and 970 cm-1 ; δH (CDCl3) 1.38(6H, t, J7.1 Hz, 2×CH2CH3), 3.70(2H, m, CH2OH), 3.89(4H, m, CH2OCH2P), 4.22(4H, m, 2×CH2CH3), 4.50(1H, m, CHON), 5.63(1H, m, D2O exchangeable, OH), 5.89(2H, br.s, D2O exchangeable, NH2), 8.18(1H, s, H-2/H-8), 8.34(1H, s, H-2/H-8); Found: C,39.58; H,5.69; N,17.69%; M+ 375.1317; C13H22N5O6P.0.9H2O requires C,39.87; H,6.08; N,17.89%; M+ 375.1308.

Workup

  1. customAfter evaporation
  2. customthe residue was chromatographed on silica eluting with ethyl acetate-methanol 5:1 affording 9-(1-diethoxyphosphorylmethoxy3-hydroxyprop-2-oxy)adenine (120 mg, 92%) as a clear gum

Sources & evidence

ORD record
ord-1ce33847ad324691acb549bd55164c88
Source dataset
uspto-grants-1991_10
Patent number
US05055458

Reaction notes

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