Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Chloride | HCID 5234 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | Boc-Beta-Ala-OSu | HCID 10684599 | — |
| Reactant | HCID 69462687 | HCID 69462687 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 86593418 | HCID 86593418 | 58.9% |
Reaction Steps
To a suspension of 1-(2-fluoroethyl)-1H-pyrazole-4,5-diamine sulfate (3 g) in tetrahydrofuran (30 ml) were added tert-butyl {3-[(2,5-dioxo-1-pyrrolidinyl)oxy]-3-oxopropyl}carbamate (3.9 g) and N,N-diisoporpylethylamine (3.5 g) under ice-cooling. The reaction mixture was stirred at room temperature for 2 hours. An aqueous sodium hydrogen carbonate solution and sodium chloride were added, and the mixture was extracted with ethyl acetate-tetrahydrofuran (three times). The organic layer was dried over magnesium sulfate and concentrated in vacuo. The residue was purified by column chromatography on silica gel (ethyl acetate→ethyl acetate:ethanol=8:1) to give tert-butyl (3-{[5-amino-1-(2-fluoroethyl)-1H-pyrazol-4-yl]amino}-3-oxopropyl)carbamate (2.3 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07129232B2 |
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| Source dataset | uspto-grants-2006_10 |
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| ORD ID | ord-096a1cd3f0504a95be7ba41c1050b414 |
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| Source note | uspto-grants-2006_10 |
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