Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Methyl 3-(methylamino)but-2-enoate | HCID 2734182 | — |
| Reactant | 2-Chloro-4-fluorobenzoyl chloride | HCID 2736546 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 178483602 | HCID 178483602 | — |
Reaction Steps
To a mixture of methyl 3-(methylamino)-2-butenoate (i.e. the product of Step A) (10.25 g, 79.43 mmol) and triethylamine (13.26 mL, 9.63 g, 95.31 mmol) in toluene (125 mL) at 0° C. was added dropwise 2-chloro-4-fluorobenzoyl chloride (15.25 g, 79.48 mol) in toluene (25 mL) over 30 minutes while maintaining the temperature of the reaction mixture between about 0 to 5° C. The reaction mixture was allowed to warm to room temperature and stirred over night. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The resulting dark yellow oil was triturated with hexanes and filtered to provide the title compound as a white solid (15.91 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08754115B2 |
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| Source dataset | uspto-grants-2014_06 |
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| ORD ID | ord-c2780f1beab64aee9f3d1542d987565d |
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| Source note | uspto-grants-2014_06 |
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