Hydrazine hydrate (1:1) → HCID 21478218, compound
Reaction equation
O[CH2:2][CH2:3][N:4]1C(=O)C2=CC=CC=C2C1=O.[SH:15][C:16]1[S:17][C:18]2[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=2[N:20]=1.O.NN.C(O[C@@H]1[C@H](OC(=O)C)[C@@H](COC(=O)C)O[C@H]1N1C=NC2C1=NC(Cl)=NC=2[Cl:55])(=O)C.C[O-].[Na+]>CO>[ClH:55].[ClH:55].[S:17]1[C:18]2[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=2[N:20]=[C:16]1[S:15][CH2:2][CH2:3][NH2:4]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
2-(2-Benzothiazolylthio)ethylamine dihydrochloride was prepared by standard synthetic steps with a by Mitsunobu reaction between N-(2-hydroxyethyl)phthalimide and 2-mercaptobenzothiazole, followed by reaction with hydrazine hydrate. This amine dihydrochloride (0.52 g, 2.11 mmol) was reacted with 9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-2,6-dichloro-9H-purine (0.79 g, 1.7 mmol), followed by deacylation of the purified 2',3',5'-tri-O-acetyl-N-[(R)-2(2-benzothiazolylthio)-1-ethyl]-2-chloroadenosine using sodium methoxide in methanol to provide the title N-[(R)-2-(2-benzothiazolylthio)-1-ethyl]-2-chloroadenosine as a foam after column chromatography, 1H NMR (DMSO-D6) δ3.54-3.60 and 3.64-3.71 (4H, m, H-5'a and H-5'b and --CH2 --), 3.42, (2H, q, --CH2 --), 3.96 (1H, d, H-4'), 4.15 (1H, q, H-3'), 4.52 (1H, q, H-2'), 5.08 (1H, t, 5'-OH), 5.22, 5.51 (2H, 2d, 2'- and 3'-OH), 5.85 (1H, d, H-1'), 7.38, 7.48 (2H, 2t, Ar--H), 7.85, 8.02 (2H, 2d, Ar--H), 8.43 (1H, s, H-8), 8.68 (1H, t, N--H). HPLC retention time 18.5 min [gradient elution, 20-80% acetonitrile/water (containing 0.1% TFA)].
Sources & evidence
- ORD record
- ord-4ec74e754fd44d25a0c0b4c8d7ba6d75
- Source dataset
- uspto-grants-1997_11
- Patent number
- US05683989
Reaction notes
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