Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Dimethyl Sulfate | HCID 6497 | — |
| Reactant | 1,8-Diazabicyclo(5.4.0)undec-7-ene | HCID 81184 | — |
| Reactant | HCID 86589031 | HCID 86589031 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 86589032 | HCID 86589032 | — |
Reaction Steps
The product of Step 1 (2.50 g) is dissolved in DMF (11 mL) and cooled to 0° C. DBU (1.68 g) is added, followed by dimethyl sulphate (953 mg) after 10 minutes. The reaction is stirred at room temperature for 2 hours, poured into water and extracted with ethyl acetate. The combined organic phases are washed with water and brine, then dried over sodium sulfate. Evaporation affords 5-methylpyrazine-2 carboxylic acid (6S,9S,10S,11S,13S,16R,17R)-9,11-epoxy-6-fluoro-17-methoxycarbonyl-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl ester. Observed mass (M+H) 511.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US06921757B2 |
|---|
| Source dataset | uspto-grants-2005_07 |
|---|
| ORD ID | ord-21bb32829d0f4bc6bbc2823fd783f36e |
|---|
| Source note | uspto-grants-2005_07 |
|---|
