Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Isopropanol | HCID 3776 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | acetic acid (2R,3R,4R,5R)-4-acetoxy-2-(2,6-dichloro-purin-9-yl)-5-(2-ethyl-2H-tetrazol-5-yl)-tetrahydro-furan-3-yl ester | HCID 12151756 | — |
| Reactant | HCID 178449843 | HCID 178449843 | — |
| Product | HCID 178463187 | HCID 178463187 | — |
Reaction Steps
To stirred (2R,3R,4R,5R)-2-(2,6-dichloro-9H-purin-9-yl)-5-(2-ethyl-2H-tetrazol-5-yl)tetrahydrofuran-3,4-diyl diacetate (ref WO98/28319A1) (15 g) in propan-2-ol (100 ml) was added N,N-diisopropylethylamine (7.7 ml) and 1,1-dimethylethyl(trans-4-aminocyclohexyl)carbamate (6.82 g). The mixture was stirred at 65° C. for 24 h before cooling to room temperature and concentrating in vacuo. The crude product was purified by column chromatography (silica) eluting with 30% cyclohexane in ethyl acetate. The appropriate fractions were combined and concentrated in vacuo and triturated with diethyl ether to yield the title compound as a white solid, 8.56 g.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07985740B2 |
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| Source dataset | uspto-grants-2011_07 |
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| ORD ID | ord-83fc0dc278cf45f585b5466307d90732 |
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| Source note | uspto-grants-2011_07 |
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