Formic Acid → HCID 136072601, compound
Reaction equation
Cl[C:2]1[N:10]=[C:9]([NH:11]C=O)[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[O:14][CH2:15][CH:16]([CH2:27][O:28]C(=O)C)[CH2:17][CH2:18][P:19]([O:24][CH2:25][CH3:26])([O:21][CH2:22][CH3:23])=[O:20].C(O)=[O:33]>>[OH:28][CH2:27][CH:16]([CH2:17][CH2:18][P:19]([O:24][CH2:25][CH3:26])([O:21][CH2:22][CH3:23])=[O:20])[CH2:15][O:14][N:6]1[CH:5]=[N:4][C:3]2[C:2](=[O:33])[NH:10][C:9]([NH2:11])=[N:8][C:7]1=2Participants
Conditions
- Temperature
- 90 °C
Procedure
A solution of 6-chloro-9-[2-(acetoxymethyl)-4-(diethoxyphosphoryl)butoxy]-2-formamidopurine (0.128 g, 0.268 mmol) in 80% formic acid (5 ml) was stirred at 80° C. for 5 hours. The solvent was evaporated under reduced pressure and the residue coevaporated with toluene (2×10 ml). The residue was redissolved in a 0.02 M solution of hydrochloric acid in ethanol (4ml) and the resulting mixture stirred at 90° C. for 2 hours. The solvents were evaporated under reduced pressure and the residue coevaporated with ehtanol (2×15 ml). The product was purified by column chromatography on silica gel (eluting with chloroform:ethanol 92:8) to give the title compound (64 mg, 61%). 1H NMR: δH [(CD3)SO] 1.22 (6H, t, J=7Hz, (CH3CH2 ()2), 1.75 (5H, m, CHCH2CH2P), 3.5 (2H, m, CH2OH), 4.0 (4H, m, (OCH2CH3)2), 4.24 (2H, m, NOCH2), 4.64 (1H, t, J=5.2Hz, D2O exchangeable, CH2OH), 6.55 (2H, br.s, D2O exchangeable, NH2), 7.92 (1H, s, H-8), 10.52 (1H, br.s, D2O exchangeable, NH).
Workup
- customThe solvent was evaporated under reduced pressure
- dissolutionThe residue was redissolved in a 0.02 M solution of hydrochloric acid in ethanol (4ml)
- customThe solvents were evaporated under reduced pressure
- customThe product was purified by column chromatography on silica gel (eluting with chloroform:ethanol 92:8)
Sources & evidence
- ORD record
- ord-6ef068b58d884e0e84940f24362b7c5a
- Source dataset
- uspto-grants-1992_11
- Patent number
- US05166198
Reaction notes
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