HuagongsheHuagongshe Chemistry Print Report · For research reference only
1,2-Dichloroethane → (S)-2-(3-{3-[[2-Chloro-3-(trifluoromethyl)benzyl](2-phenyl-propyl)amino]propoxy}-phenyl)-acetamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1,2-Dichloroethane | HCID 11 | — |
| Reactant | Ammonia | HCID 222 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1-Hydroxybenzotriazole hydrate | HCID 2796029 | — |
| Reactant | (S)-2-(3-{3-[(2-Chloro-3-(trifluoromethyl)benzyl](2-phenyl-propyl)amino]propoxy}-phenyl)acetic acid hydrochloride salt | HCID 68817123 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | (S)-2-(3-{3-[[2-Chloro-3-(trifluoromethyl)benzyl](2-phenyl-propyl)amino]propoxy}-phenyl)-acetamide | HCID 10289382 | 60% |
Reaction Steps
To a solution (S)-2-(3-{3-[[2-chloro-3-(trifluoromethyl)benzyl](2-phenyl-propyl)amino]propoxy}-phenyl)acetic acid hydrochloride salt (50 mg, 0.1 mmol) in dichloromethane, 1,2-dichloroethane (EDC, 19.2 mg, 0.1 mmol), 1-hydroxybenzotriazole hydrate (HOBT, 13.6 mg, 0.1 mmol), triethylamine (Et3N, 14 μl, 0.1 mmol) and ammonia (1.0M in dioxane, 0.24 ml) were added. After the resulting mixture was stirred at room temperature for over night it was washed with 0.1N HCl, saturated NaHCO3, water and brine. The organic layer was dried over Na2SO4 and concentrated under vacuum. The residue was purified with HPLC to give the tittle compound as a light yellow oil 30 mg, yield 60%. MS m/e 519.0 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07247748B2 |
| Source dataset | uspto-grants-2007_07 |
| ORD ID | ord-f45395959e8946d2ba8ce60dd85908a4 |
| Source note | uspto-grants-2007_07 |