Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 3-(Trifluoromethyl)benzoic acid | HCID 9963 | — |
| Reactant | O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate | HCID 2733207 | — |
| Reactant | HCID 68769972 | HCID 68769972 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 68765645 | HCID 68765645 | — |
| Product | HCID 68766300 | HCID 68766300 | 104.1% |
Reaction Steps
To a solution of (S)-3-amino-1-((1S,2R,4R)-2-(1-hydroxypropyl)-4-(isopropyl(methyl)amino)cyclohexyl)pyrrolidin-2-one (47.6 mg, 0.153 mmol) in CH3CN (2 mL) were added triethylamine (0.08 mL, 0.46 mmol), 3-trifluoromethylbenzoic acid (38 mg, 0.2 mmol), and TBTU (73.7 mg, 0.23 mmol), and the mixture was stirred for 8 h at rt. The reaction mixture was diluted with EtOAc, and washed with 1N—NaOH and water. The organic layer was dried (Na2SO4), filtered, and concentrated in vacuo. The residue was purified by flash chromatography on silica gel with elution by 0.8:7.2:92 cNH4OH-MeOH—CH2Cl2 to afford the titled compound N-(1-((1S,2R,4R)-2-((R)-1-hydroxypropyl)-4-(isopropyl(methyl)amino)cyclohexyl)-2-oxopyrrolidin-3-yl)-3-(trifluoromethyl)benzamide (38.5 mg) as a solid. MS found: (M+H)+=484.3.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07163937B2 |
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| Source dataset | uspto-grants-2007_01 |
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| ORD ID | ord-23b437ccd99e4f3cb6c270cb789e5a89 |
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| Source note | uspto-grants-2007_01 |
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