Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Thionyl Chloride | HCID 24386 | — |
| Reactant | [(2S,4R,5R)-4-acetyloxy-5-(6-oxo-3H-purin-9-yl)oxolan-2-yl]methyl acetate | HCID 178476341 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 10915235 | HCID 10915235 | 89.9% |
Reaction Steps
32.7 g (97.2 mmols) of 2′,5′-di-O-acetyl-3′-deoxyinosine was suspended in 449 ml of methylene chloride in a 1-liter reactor, to which were added 30.1 ml (389 mmols) of dimethylformamide and 28.0 ml (389 mmols) of thionyl chloride, and reacted for about 7 hours while heating under reflux. The reaction mixture was cooled to 0° C., and then dropwise added to 500 ml of water that had been cooled at 0° C. to stop the reaction. The reaction mixture was separated into layers, and the organic layer was taken out, and washed with water, an aqueous saturated solution of sodium hydrogencarbonate and a saturated saline solution in that order. The solvent was evaporated, and 31.0 g of an oily product was obtained. This crude product was directly subjected to the next reaction.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06500946B1 |
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| Source dataset | uspto-grants-2002_12 |
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| ORD ID | ord-37833eba26b1447eb1a44e4641e13976 |
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| Source note | uspto-grants-2002_12 |
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