Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 3-(1,1-Dimethylethyl) 9-(carboxyfluoromethylene)-3-azabicyclo[3.3.1]nonane-3-carboxylate | HCID 68443169 | — |
| Reactant | HCID 86597098 | HCID 86597098 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Solvent | Dimethylacetamide | HCID 31374 | — |
| Product | HCID 68440920 | HCID 68440920 | — |
Reaction Steps
69 μl of DIEA are added to a solution of 60 mg of 9-(carboxy-fluoro-methylene)-3-aza-bicyclo[3.3.1]nonane-3-carboxylic acid tert-butyl ester, 71 mg of 2,4,5-trichloro-thiophene-3-sulfonyl amide, 233 μl of PPA and 24 mg of DMAP in 2 ml of DMA, and the mixture obtained is stirred at 40° overnight. The mixture obtained is diluted with 10 ml of EtAc/c-HEX, and washed with 1M NaHSO4 solution. The organic layer obtained is dried and solvent is evaporated. The evaporation residue obtained is subjected to chromatography on silica gel and on Sephadex LH20 (MeOH) and relevant fractions obtained from chromatography are subjected to lyophilisation from dioxane. 9-[1-Fluoro-2-oxo-2-(2,4,5-trichloro-thiophene-3-sulfonylamino)-ethylidene]-3-aza-bicyclo[3.3.1]nonane-3-carboxylic acid tert.-butyl ester in the form of a powder is obtained.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07482462B2 |
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| Source dataset | uspto-grants-2009_01 |
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| ORD ID | ord-18b7bf5dd91b40b7bc510b7cfdf6470c |
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| Source note | uspto-grants-2009_01 |
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