HCID 19993533, compound → HCID 19993505, compound

HRID 345068Notes

Reaction equation

HRID 345068 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][CH2:19][CH:20]([O:32][Si](C(C)(C)C)(C)C)[CH2:21][O:22][CH2:23][P:24]([O:29][CH2:30][CH3:31])([O:26][CH2:27][CH3:28])=[O:25])=[C:11]([O:40][CH3:41])[N:10]=1)=O)(C)(C)C>C(O)(=O)C>[NH2:8][C:9]1[N:17]=[C:16]2[C:12]([N:13]=[CH:14][N:15]2[O:18][CH2:19][CH:20]([OH:32])[CH2:21][O:22][CH2:23][P:24]([O:26][CH2:27][CH3:28])([O:29][CH2:30][CH3:31])=[O:25])=[C:11]([O:40][CH3:41])[N:10]=1

Participants

3

Reactant 1

HCID 19993533HCID 19993533, compound

Product 1

HCID 19993505HCID 19993505, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 2-[bis(t-butoxycarbonyl)amino]-9-[2-(t-butyldimethylsilyloxy)-3-(diethoxyphosphorylmethoxy) propoxy]-6-methoxypurine (0.66 g, 0.91 mmol) in 80% acetic acid (25 ml) was stirred at 85° C. for 4 h. The solution was evaporated in vacuo and the residue chromatographed on silica, eluting with chloroformmethanol 25:1, affording 2-amino-9-[3-(diethoxyphosphorylmethoxy)-2-hydroxypropoxy)-6-methoxypurine (275mg, 75%) as a clear gum. νmax (film) 3460, 3340, 1640, 1580, 1460 and 1390 cm-1 ; δH (CDCl3) 1.34 (6H, t, J6.9 Hz, 2×CH3CH2), 3.75 (2H, m, CH2OCH2P), 3 89 (2H, d, J7.7 Hz, CH2P), 4.04 (1H, m, CHOH), 4.09 (3H, s, OCH3), 4.17 (4H, m, 2×CH3CH 2), 4.34 (2H, m, CH2ON), 5.09 (2H, br.s, D2O exchangeable, NH2), 7.78 (1H, s, H-8). Found: C, 40.67; H, 6.18, N, 16.54%; M+ 405.1413. C14H24N5O7P.0.5H2O requires C, 40.58; H, 6.08; N, 16.90%; M+ 405.1413.

Workup

  1. customThe solution was evaporated in vacuo
  2. customthe residue chromatographed on silica
  3. washeluting with chloroformmethanol 25:1

Sources & evidence

ORD record
ord-ccaa011db9594e238e6cabba1cf5881e
Source dataset
uspto-grants-1991_10
Patent number
US05055458

Reaction notes

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