Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | 1,1'-Carbonyldiimidazole | HCID 68263 | — |
| Reactant | 1,8-Diazabicyclo(5.4.0)undec-7-ene | HCID 81184 | — |
| Reactant | Cyclopropanesulfonamide | HCID 15765418 | — |
| Reactant | HCID 67103077 | HCID 67103077 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 70324238 | HCID 70324238 | 73% |
Reaction Steps
(1R,2R)-1-(tert-butoxycarbonyl)-2-ethylcyclopropanecarboxylic acid (0.5 g, 2.18 mmol) was dissolved in THF (20 mL), followed by addition of CDI (390 mg, 2.41 mmol) in one portion at rt. The reaction was stirred in a 60° C. sandbath for 4 h, cooled to rt, and cyclopropanesulfonamide (292 mg, 2.41 mmol) and DBU (366 mg, 2.41 mmol) were added. The reaction was stirred at rt for overnight. The reaction was then diluted with EtOAc (30 mL) and washed with 1 N HCl (2×15 mL), water (10 mL), brine (10 mL), and dried (Na2SO4), giving tert-butyl (1R,2R)-1-(cyclopropylsulfonylcarbamoyl)-2-ethylcyclopropylcarbamate (0.53 g, 73% yield) as a white solid after removal of solvent. This crude product was directly used for the next without further purification.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07932277B2 |
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| Source dataset | uspto-grants-2011_04 |
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| ORD ID | ord-b5483f3d50344e079b05830a57500f96 |
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| Source note | uspto-grants-2011_04 |
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