Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Trifluoroacetic anhydride | HCID 9845 | — |
| Reactant | HCID 68709601 | HCID 68709601 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 68711938 | HCID 68711938 | 50% |
Reaction Steps
(2S)-1-(2-(N-tert-Butyloxycarbonyl-N-(2-methylpropyl)amino)acetyl)pyrrolidine-2-carboxamide (330 mg, 1.01 mmol) was dissolved in dry THF (20 ml). The solution was cooled to 0° C., triethylamine (210 mg, 2.1 mmol) was added followed by the slow addition of trifluoroacetic anhydride (460 g, 2.2 mmol). The pH was adjusted to pH9 with triethylamine. After 30 min the reaction mixture was diluted with ethyl acetate (100 ml), washed with water and brine, dried (Na2SO4) and evaporated in vacuo. The residue was purified by flash chromatography (eluant: 3% methanol, 97% chloroform) to give an orange oil identified as the title compound (156 mg, 0.50 mmol, 50%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08183280B2 |
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| Source dataset | uspto-grants-2012_05 |
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| ORD ID | ord-5457260f24f94c2bb0bd8de5074efb37 |
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| Source note | uspto-grants-2012_05 |
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