Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetonitrile | HCID 6342 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Methyl Isocyanate | HCID 12228 | — |
| Reactant | HCID 57213576 | HCID 57213576 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | HCID 57124693 | HCID 57124693 | 22% |
Reaction Steps
0.15 ml of triethylamine and 60 μl of methylisocyanate were added to an acetonitrile solution containing 200 mg of a known (4aS,6S,7R,7aR)-6,7-epoxy-1,4a,5,6,7,7a-hexahydro-1-hydroxy-7-methylcyclopenta [c] pyrane-4-carboxylic acid methylester followed by stirring for 1 hour at room temperature. After adding 1 ml of methanol to the reaction mixture, it was concentrated under reduced pressure. The residue was purified by silica gel chromatography to obtain colorless needles from the hexane-ether eluate in the form of (1S,4aS,6S,7R,7aR)-6,7-epoxy-1,4a,5,6,7,7a-hexahydro-1-methylcarbamoyloxy-7-methylcyclopenta [c] pyrane-4-carboxylic acid methylester (55 mg, yield : 22%). The physicochemical properties of this compound are described in Table 1, Compound No. 3).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06225478B1 |
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| Source dataset | uspto-grants-2001_05 |
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| ORD ID | ord-ca60f2227d9f42b995c9384cb3c45ef2 |
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| Source note | uspto-grants-2001_05 |
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