Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Butylamine | HCID 8007 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Diethyl cyanophosphonate | HCID 76257 | — |
| Reactant | HCID 57046261 | HCID 57046261 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 86754331 | HCID 86754331 | — |
Reaction Steps
A solution of 100 mg (0.19 mmol) of 4-[N-(3,5-bistrifluoromethyl-benzoyl)-N-methyl-amino]-5,5-diphenyl-pent-2-enoic acid and 37 μl (0.27 mmol) of triethylamine in 3 ml of N,N-dimethylformamide at 0° C. is treated with 23 μl (0.23 mmol) of butylamine, followed by 38 μl (0.23 mmol) of diethyl cyanophosphonate. After stirring for 4 h at room temperature, the reaction mixture is concentrated, diluted with ethyl acetate, and then washed with saturated sodium bicarbonate solution. The aqueous layer is further extracted with ethyl acetate (3×). The organic layers are combined, dried with sodium sulfate and concentrated. The residue is then purified by flash chromatography (95:5 methylene chloride/methanol) to give the title compound as a white solid. TLC: methylene chloride/methanol (95:5) Rf =0.23.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US05929067 |
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| Source dataset | uspto-grants-1999_07 |
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| ORD ID | ord-518e569eab6f47f4b6432be808e49070 |
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| Source note | uspto-grants-1999_07 |
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