Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Diethyl cyanophosphonate | HCID 76257 | — |
| Reactant | 2-Chloro-4-propoxybenzoic acid | HCID 22494326 | — |
| Reactant | HCID 86596097 | HCID 86596097 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 10298335 | HCID 10298335 | 60.9% |
Reaction Steps
To a solution of 0.091 g of methyl 2-[3-(ammoniomethyl)-4-methoxybenzyl]tetrahydro-2-furancarboxylate chloride and 0.074 g of 2-chloro-4-propoxybenzoic acid in 2.5 ml of N,N-dimethylformamide were added 0.119 μl of triethylamine and 0.119 μl of diethyl cyanophosphonate, and the mixture was stirred at room temperature for 4 hours. 10 ml of water and 10 ml of ethyl acetate were added, and the organic layer was evaporated. The residue was dissolved in 2.5 ml of ethanol, 0.3 ml of 5N sodium hydroxide was added, and the mixture was stirred at room temperature for 14 hours. The reaction mixture was concentrated, and 5 ml of ethyl acetate, 2.5 ml of water and 0.5 ml of 5N hydrochloric acid were added. The organic layer was concentrated, and the residue was purified by HPLC, to give 0.081 g of the title compound as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07371777B2 |
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| Source dataset | uspto-grants-2008_05 |
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| ORD ID | ord-1524615ae3ce4aaf87289c00fa09a554 |
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| Source note | uspto-grants-2008_05 |
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