Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Butyric Acid | HCID 264 | — |
| Reactant | Dicyclohexylcarbodiimide | HCID 10868 | — |
| Reactant | (R)-9-[4-(N-tert-Butoxycarbonyl-L-valyloxy)-2-hydroxymethylbutyl]guanine | HCID 136201790 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 136110737 | HCID 136110737 | 34.4% |
Reaction Steps
DCC (110 mg, 0.53 mmol) was dissolved in dichloromethane (10 ml) and butyric acid (82 mg, 0.93 mmol) was added. After 4 hours at room temperature the mixture was filtered and the filtrate was evaporated. The residue was dissolved in pyridine (5 ml) and (R)-9-[4-(N-tert-Butoxycarbonyl-L-valyloxy)-2-hydroxymethylbutyl]guanine (200 mg, 0.44 mmol) (Example 1, step a) was added. The mixture was stirred for 120 hours at room temperature. According to TLC the reaction was incomplete and more anhydride was made using the procedure above. This anhydride was added and the mixture was stirred for an additional 20 hours. The reaction mixture was evaporated and chromatographed first on silica gel and then on aluminium oxide, in both cases eluted with dichloromethane/methanol to give 79 mg of the intermediate product.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07189849B2 |
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| Source dataset | uspto-grants-2007_03 |
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| ORD ID | ord-0369146dcd964448931ce0d607da4298 |
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| Source note | uspto-grants-2007_03 |
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