Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Propargyl bromide | HCID 7842 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | HCID 86588809 | HCID 86588809 | — |
| Solvent | Chloroform | HCID 6212 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 86588808 | HCID 86588808 | 56% |
Reaction Steps
The TFA salt (403a) (92 mg, 0.15 mmol) was dissolved in 2 mL of chloroform and the solution was cooled to 0° C. Triethylamine (88 mg, 122 μL, 0.87 mmol) and propargyl bromide (65 mg, 50 μL, 0.44 mmol) were added subsequently. The mixture was stirred until disappearance of compound (403a). The solution was diluted with ethyl acetate and washed with H2O and brine, and dried over MgSO4. After filtration and concentration, the residue was purified on silica gel to provide methyl (3S,4S)-4-({4-[(2-methyl-4-quinolinyl)methyl]benzoyl}amino)-1-(2-propynyl)-3-pyrrolidinecarboxylate (36 mg, 56%). MS (AP+): 442 (M+1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06740649B2 |
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| Source dataset | uspto-grants-2004_05 |
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| ORD ID | ord-20b53d7c7cef471a8102fe259bdd1dcf |
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| Source note | uspto-grants-2004_05 |
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