Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | HCID 131723754 | HCID 131723754 | — |
| Catalyst | Tetrakis(triphenylphosphine)palladium | HCID 11979704 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 69159146 | HCID 69159146 | — |
Reaction Steps
To a stirring solution of methyl (2E)-5-{N-[(3-amino-6-bromophenyl)methyl](tert-butoxy)carbonylamino}pent-2-enoate (1 eq) in toluene (0.08 M) at room temperature was added tetrakis(triphenylphosphine) palladium(0.03 eq) and triethylamine (3 eq). The reaction mixture was stirred at 100° C. for 18 hr and filtered through celite. The reaction solvent was removed by rotary evaporation. The residue was partitioned between ethyl acetate and saturated sodium bicarbonate. The organic phase was separated, washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash chromatography (30% EtOAc/Hexane). EI-MS m/z 333 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US06514964B1 |
|---|
| Source dataset | uspto-grants-2003_02 |
|---|
| ORD ID | ord-ebb3af524d694fdeb3fbeb4d28ba2a43 |
|---|
| Source note | uspto-grants-2003_02 |
|---|