Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | (+-)-Tetrahydro-2-furoic acid | HCID 86079 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | HCID 117621853 | HCID 117621853 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 66750896 | HCID 66750896 | 59.1% |
Reaction Steps
To a stirred solution of 2-tetrahydrofuroic acid (23 mg, 0.2 mmol) in DMF (0.5 mL) was added N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (38 mg, 0.2 mmol) and HOBt (27 mg, 0.2 mmol) in DMF (0.25 mL) followed by 1 (2-(tert-butylphenyl)piperazine dihydrochloride (29 mg, 0.1 mmol) with triethylamine (0.014 mL, 0.2 mmol) in DMF (0.25 mL). After stirring for 15 h at room temperature, saturated sodium hydrogen carbonate solution (1.5 mL) was added to the mixture, and the mixture was extracted with ethyl acetate (2 mL). The organic layer was separated by phase separation filter kit and the filtrate was evaporated under reduced pressure. The resulting residue was dissolved in dimethylsulfoxide (1 mL) and the solution was purified by preparative HPLC. The eluted fraction was evaporated by air blowing at 60° C. to give the title compound (18.7 mg, 59%). LC/MS (ESI+) m/z: 317 (M+H)+. purity 100%.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08853215B2 |
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| Source dataset | uspto-grants-2014_10 |
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| ORD ID | ord-cb1c03be726d4326a99fbc25a5e6f2a9 |
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| Source note | uspto-grants-2014_10 |
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