Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 3-(Trifluoromethyl)phenyl isocyanate | HCID 9483 | — |
| Reactant | HCID 178525089 | HCID 178525089 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 178516687 | HCID 178516687 | 92.9% |
Reaction Steps
3-trifluoromethyl-phenylisocyanate (11 mg, 1.2 eq.) is added to a solution of benzyl (2S)-2-[(1H-indol-3-ylmethyl)amino]-4-(4-phenyl-1H-imidazol-2-yl)butanoate (23 mg, 1 eq.) in 2 ml of THF. The mixture is stirred for 2 hours at approximately 20° C. then diluted with 2 ml of THF. Aminomethylpolystyrene resin (acquired from Novabiochem, load 3.2 mmol/g, 125 mg, 2 eq.) is added, then triethylamine (200 μl). The mixture is stirred for 15 hours at approximately 20° C. then filtered on frit. The filtrate is then concentrated to dryness under reduced pressure at 40° C. (a co-evaporation with dichloromethane is necessary to eliminate the excess triethylamine) in order to produce the expected compound (25 mg, 92% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07199145B2 |
|---|
| Source dataset | uspto-grants-2007_04 |
|---|
| ORD ID | ord-83f75943b7454b2faace6013fa2c8db2 |
|---|
| Source note | uspto-grants-2007_04 |
|---|