HuagongsheHuagongshe Chemistry Print Report · For research reference only
Potassium Carbonate → (2r)-[t-Butyloxycarbonyl(4'-chlorobiphenyl-4-sulfonyl)amino]-4-(3,4,4-trimethyl-2,5-dioxoimidazolidin-1-yl)butyric acid t-butyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 1,5,5-Trimethylimidazolidine-2,4-dione | HCID 81295 | — |
| Reactant | (2R)-[t-butyloxycarbonyl(4'-chlorobiphenyl-4-sulfonyl)amino]-4-iodobutyric acid t-butyl ester | HCID 53729423 | — |
| Catalyst | 18-Crown-6 | HCID 28557 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | (2r)-[t-Butyloxycarbonyl(4'-chlorobiphenyl-4-sulfonyl)amino]-4-(3,4,4-trimethyl-2,5-dioxoimidazolidin-1-yl)butyric acid t-butyl ester | HCID 69287681 | 41% |
Reaction Steps
To a solution of the title F compound, (2R)-[t-butyloxycarbonyl(4′-chlorobiphenyl-4-sulfonyl)amino]-4-iodobutyric acid t-butyl ester (0.6 g, 0.94 mmol) in 10 mL DMF is added 3,4,4-trimethyl-2,5-dioxoimidazolidine and potassium carbonate (0.65 g, 4.72 mmol) followed by 2 mg of 18-crown-6. The reaction mixture is stirred at room RT for 3 h, then partitioned between water and EtOAc. The organic solution is washed with brine, dried over anhydrous Na2SO4 and concentrated. Chomatography on silica gel (eluant; 1/19—EtOAc/hexane) affords the title compound as a white foam (0.25 g, 41%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06410580B1 |
| Source dataset | uspto-grants-2002_06 |
| ORD ID | ord-99c838b5a3b542dc8d4c75a00fe71ce3 |
| Source note | uspto-grants-2002_06 |