HuagongsheHuagongshe Chemistry Print Report · For research reference only
Toluene → 2-{2-[2-(1-Carboxy-2-methyl-butylcarbamoyl)-6-fluoro-phenyldisulfanyl]-3-fluoro-benzoylamino}-3-methyl-pentanoic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Toluene | HCID 1140 | — |
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | Anisole | HCID 7519 | — |
| Reactant | 2-[2-[2-(1-Tert-butoxycarbonyl-2-methyl-butylcarbamoyl)-6-fluorophenyldisulfanyl]-3-fluoro-benzoylamino]-3-methylpentanoic acid tert butyl ester | HCID 76125851 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 2-{2-[2-(1-Carboxy-2-methyl-butylcarbamoyl)-6-fluoro-phenyldisulfanyl]-3-fluoro-benzoylamino}-3-methyl-pentanoic acid | HCID 53792067 | 44% |
Reaction Steps
To a solution of [S-(R*,R*)]-2-[2-[2-(1-tert-butoxycarbonyl-2-methyl-butylcarbamoyl)-6-fluorophenyldisulfanyl]-3-fluoro- benzoylamino]-3-methylpentanoic acid tert butyl ester (0.6 g ,0.8 mmol) and anisole (1 ml) in 10 mL dichloromethane at 0° C., was added dropwise 10 mL trifluoroacetic acid. The mixture was allowed to warm to ambient temperature. After 4 hours, 5 mL toluene was added and the solvents were removed in vacuo. The crude product was recrystallized from methanol/water to yield 0.2 g of the title compound, mp 188°-190° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05734081 |
| Source dataset | uspto-grants-1998_03 |
| ORD ID | ord-58247be6c9cf4f31b764ec27ffb99a3b |
| Source note | uspto-grants-1998_03 |