Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Cyclohexanecarbonyl chloride | HCID 75938 | — |
| Reactant | HCID 70570127 | HCID 70570127 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Solvent | Sodium Bicarbonate | HCID 516892 | — |
| Product | HCID 70572676 | HCID 70572676 | 99.8% |
Reaction Steps
tert-Butyl (2-{[(4′-aminobiphenyl-3-yl)methyl](methyl)amino]-2-oxoethyl}carbamate (240 mg) was dissolved in a mixed solution of EtOAc (10 ml)/saturated aqueous sodium hydrogen carbonate solution (10 ml), followed by ice-cooling. A solution of cyclohexanecarbonyl chloride (142 mg) in EtOAc (5 ml) was added dropwise thereto. The reaction mixture was returned to room temperature and stirred for 24 hours, and then to the reaction mixture was added water, followed by extraction with EtOAc. The organic layer was dried over MgSO4 and evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (EtOAc/hexane=2/1) to obtain tert-butyl {2-[({4′-[(cyclohexylcarbonyl)amino]biphenyl-3-yl}methyl)(methyl)amino]-2-oxoethyl}carbamate (311 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08802679B2 |
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| Source dataset | uspto-grants-2014_08 |
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| ORD ID | ord-b7c6d0a5a10d47bbaa1ea8058207d4cb |
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| Source note | uspto-grants-2014_08 |
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