Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | O-Xylene | HCID 7237 | — |
| Reactant | Ammonia acetate | HCID 12432 | — |
| Reactant | 1,1-Dimethylethyl (2S)-2-[[[2-(4-bromophenyl)-2-oxoethyl]amino]carbonyl]-4,4-difluoro-1-pyrrolidinecarboxylate | HCID 59166348 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 57611030 | HCID 57611030 | 102.8% |
Reaction Steps
In a 50 mL seal tube, (S)-tert-butyl 2-(2-(4-bromophenyl)-2-oxoethylcarbamoyl)-4,4-difluoropyrrolidine-1-carboxylate (1.8 g, 4.02 mmol) and acetic acid, ammonia acetate salt (1.55 g, 20.1 mmol) were combined with xylene (16 ml). The reaction mixture was heated to 140° C. and stirred for 4 hr. The reaction mixture was cooled and diluted with EtOAc (50 ml). It was washed with water and brine, dried with MgSO4, concentrated and purified on a silica gel column (CH2Cl2, 30%, 50%, 80% EtOAc/CH2Cl2) to afford (S)-tert-butyl 2-(5-(4-bromophenyl)-1H-imidazol-2-yl)-4,4-difluoropyrrolidine-1-carboxylate as a yellow solid (1.77 g, 74%): ESI-LRMS m/e calcd for C18H22BrF2N3O2 [M+] 428. found 429 [M+H+].
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09180193B2 |
|---|
| Source dataset | uspto-grants-2015_11 |
|---|
| ORD ID | ord-8bf8f2abd84541d795828cc9dc807833 |
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| Source note | uspto-grants-2015_11 |
|---|
