Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Citric Acid | HCID 311 | — |
| Reactant | Aminoisobutyric acid | HCID 6119 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 2-Acetylcyclohexanone | HCID 13400 | — |
| Reactant | 4-Bromo-N-tert-butyl-2-fluorobenzamide | HCID 22336252 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 66731962 | HCID 66731962 | 108.9% |
Reaction Steps
The title compound was prepared according to General Method 7. N-tert-butyl-4-bromo-2-fluorobenzamide (850 mg, 3.1 mmol), 2-aminoisobutyric acid (450 mg, 4.36 mmol), CuI (100 mg, 0.5 mmol), TEA (0.2 mL) and K2CO3 (1.0 g, 7.2 mmol) were charged in DMF (8 ml) and water (2 ml) and stirred at RT for 5 min. 2-acetylcyclohexanone (100 mg, 0.7 mmol) was added and the reaction mixture was heated at 100° C. for 18 h. The reaction mixture was acidified with 1 M citric acid (pH 4) and extracted with ethyl acetate (50 mL, 2 times). The combined organic layer was dried over Na2SO4 and concentrated to obtain 1.0 g of 2-(4-(tert-butylcarbamoyl)-3-fluorophenylamino)-2-methylpropanoic acid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08710086B2 |
|---|
| Source dataset | uspto-grants-2014_04 |
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| ORD ID | ord-eccd69e3ca9f4232aba44f6cc84e6489 |
|---|
| Source note | uspto-grants-2014_04 |
|---|
