HuagongsheHuagongshe Chemistry Print Report · For research reference only
1,2-Dichloroethane → (R)-N-(tert-Butoxycarbonyl)-4-[(1-methyl-2,2,2-trifluoro-ethylcarbamoyl)-methyl]-benzylamine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1,2-Dichloroethane | HCID 11 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | 2-(4-((((Tert-butoxy)carbonyl)amino)methyl)phenyl)acetic acid | HCID 2755983 | — |
| Reactant | (2R)-1,1,1-Trifluoropropan-2-amine--hydrogen chloride (1/1) | HCID 44593757 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | (R)-N-(tert-Butoxycarbonyl)-4-[(1-methyl-2,2,2-trifluoro-ethylcarbamoyl)-methyl]-benzylamine | HCID 58495584 | 68.3% |
Reaction Steps
Dissolve [4-(tert-butoxycarbonylamino-methyl)-phenyl]-acetic acid (190 mg, 0.63 mmol) in DCM (12.4 mL) and add triethylamine (354 μL, 2.5 mmol), DMAP (8 mg, 0.063 mmol), EDC (145 mg, 0.756 mmol), HOBt (102 mg, 0.756 mmol) and (R)-1-methyl-2,2,2-trifluoro-ethylamine hydrochloride (71 mg, 0.63 mmol) under nitrogen atmosphere. Stir the reaction overnight at room temperature. Concentrate in vacuo and purify by chromatography on silica gel eluting with hexane/EtOAc (1:1 and 0:1) to obtain the desired intermediate (155 mg, 68%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08680091B2 |
| Source dataset | uspto-grants-2014_03 |
| ORD ID | ord-326b17d185d1400195a1aee386bf9c84 |
| Source note | uspto-grants-2014_03 |