Hydrazine hydrate (1:1) → 5'-Deoxy-5'-[(2-hydrazinocarbonylethyl)methylamino]-adenosine sulfate
Reaction equation
[S:1]([OH:5])([OH:4])(=[O:3])=[O:2].[NH:6]([C:8]([CH2:10][CH2:11][N:12]([CH3:32])[CH2:13][C@H:14]1[O:18][C@@H:17]([N:19]2[C:28]3[N:27]=[CH:26][N:25]=[C:23]([NH2:24])[C:22]=3[N:21]=[C:20]2C)[C@H:16]([OH:30])[C@@H:15]1[OH:31])=[O:9])[NH2:7].C(CCN(C)C[C@H]1O[C@@H](N2C3N=CN=C(N)C=3N=C2)[C@H](O)[C@@H]1O)(OCC)=O.O.NN>>[S:1]([OH:5])([OH:4])(=[O:3])=[O:2].[NH:6]([C:8]([CH2:10][CH2:11][N:12]([CH3:32])[CH2:13][C@H:14]1[O:18][C@@H:17]([N:19]2[C:28]3[N:27]=[CH:26][N:25]=[C:23]([NH2:24])[C:22]=3[N:21]=[CH:20]2)[C@H:16]([OH:30])[C@@H:15]1[OH:31])=[O:9])[NH2:7]Participants
4
Procedure
The procedure was the same as reported above for 13k using 13g (95 mg, 0.25 mmol) and hydrazine monohydrate (63 mg, 0.06 mL, 1.25 mmol): yield 39 mg (43%), MS: m/z 367 (M+H)+; 1HNMR (D2O) δ 8.47 (s, 1H, H-8), 8.45 (s, 1H, H-2), 6.17 (d, 1H, H-1′, J1′,2′=4.7 Hz), 4.90 (dd, 1H, H-2′, J2′,3′=5.2 Hz), 4.56-4.60 (bm, 1H, H-4′), 4.48 (dd, 1H, H-3′, J3′,4′=5.0 Hz), 3.82 (dd, 1H, 5′-CH2), 3.66 (dd, 1H, 5′-CH2), 3.59 (bt, 2H, N(CH3)—CH2), 2.97 (s, 3H, N—CH3), 2.86 (t, 2H, NHCO—CH2); UV λmax, nm, pH 1, 256.8 (∈ 16,600), pH 7, 258.5 (∈ 16,800), pH 13, 259.5 (∈ 17,600). Anal. (C14H22N8O4.2.0H2SO4.2.0H2O) C, H, N.
Sources & evidence
- ORD record
- ord-de545d1ea7514be6a31bb4934744ddb0
- Source dataset
- uspto-grants-2014_01
- Patent number
- US08637485B2
Reaction notes
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