Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ammonia | HCID 222 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Ethyl chloroformate | HCID 10928 | — |
| Reactant | HCID 178525720 | HCID 178525720 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 178513943 | HCID 178513943 | 59% |
Reaction Steps
A solution of trans-4-[(4-bromo-2-trifluoromethoxy-benzenesulfonylamino)-methyl]-cyclohexanecarboxylic acid (7.14 g, 15.5 mmol) and triethylamine (2.35 mL, 16.9 mmol) in THF (25 mL) was cooled to 0° C. To the mixture was added ethyl chloroformate (1.62 mL, 17 mmol) in THF (5 mL) over 10 min. After stirring at 0° C. for 15 min, aqueous ammonia (27 mL) was added dropwise and the mixture was stirred at ambient temperature for 2 hr. The mixture was concentrated under reduced pressure and the concentrate was treated with water to give a solid. The solid was filtered and washed with water and hexanes to give trans-4-[(4-bromo-2-trifluoromethoxy-benzenesulfonylamino)-methyl]-cyclohexanecarboxylic acid amide as a white solid (4.2 g, 59%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07544690B2 |
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| Source dataset | uspto-grants-2009_06 |
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| ORD ID | ord-d62e019609654c6a9df1fb9034d1d2cf |
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| Source note | uspto-grants-2009_06 |
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