Sulfuric Acid → 5'-[(4-Aminooxybutyl)methylamino]-5'-deoxy-8-oxoadenosine sulfate
Reaction equation
[S:1]([OH:5])([OH:4])(=[O:3])=[O:2].NOCCN(C)C[C@H]1O[C@@H](N2C3N=CN=C(N)C=3N=C2C)[C@H](O)[C@@H]1O.C(OC(=[N:36][O:37][CH2:38][CH2:39][CH2:40][CH2:41][N:42]([CH3:62])[CH2:43][C@H:44]1[O:48][C@@H:47]([N:49]2[C:58]3[C:52]([C:53]([N:55]=[CH:56][N:57]=3)=[NH:54])=[N:51][C:50]2=[O:59])[C@H:46]([OH:60])[C@@H:45]1[OH:61])C)C.OS(O)(=O)=O>>[S:1]([OH:5])([OH:4])(=[O:3])=[O:2].[NH2:36][O:37][CH2:38][CH2:39][CH2:40][CH2:41][N:42]([CH3:62])[CH2:43][C@H:44]1[O:48][C@@H:47]([N:49]2[C:58]3[C:52]([C:53]([N:55]=[CH:56][N:57]=3)=[NH:54])=[N:51][C:50]2=[O:59])[C@H:46]([OH:60])[C@@H:45]1[OH:61]Participants
4
Procedure
The procedure was the same as reported above for 7a using 8c (190 mg, 0.41 mmol) and 2N H2SO4 (3 mL). The compound was purified by column chromatography (elution with 4:1:0.5 chloroform:methanol:NH4OH): yield 208 mg (82%), MS: m/z 384 (M+H)+; 1HNMR (DMSO-d6) δ 10.45 (bs, 1H, 8-OH), 8.05 (s, 1H, H-2), 6.58 (bs, 2H, 6-NH2), 5.77 (d, 1H, H-1′, J1′,2′=5.0 Hz), 5.37-5.71 (bm, 2H, O—NH2), 4.83 (t, 1H, H-2′, J2′,3′=4.2 Hz), 4.18-4.29 (m, 2H, H-3′, H-4′), 3.88 (t, 2H, NH2O—CH2), 3.34-3.54 (m, 2H, 5′-CH2), 3.06 (bt, 2H, N(CH3)—CH2), 2.73 (s, 3H, N—CH3), 1.46-1.74 (bm, 4H, NH2OCH2—CH2CH2); UV λmax, nm, pH 1, 263.3 (∈ 12,200), pH 7, 268.9 (∈ 13,600), pH 13, 279.9 (∈ 15,600). Anal. (C15H25N7O5.1.9H2SO4.0.1C2H5OH.2H2O) C, H, N, S.
Workup
- customThe compound was purified by column chromatography (elution with 4:1:0.5 chloroform:methanol:NH4OH)
Sources & evidence
- ORD record
- ord-95f052bdcff748449e9d8a45ec2f5bf9
- Source dataset
- uspto-grants-2014_01
- Patent number
- US08637485B2
Reaction notes
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