HuagongsheHuagongshe Chemistry Print Report · For research reference only
1,2-Dichloroethane → 1-(tert-butoxycarbonyl)-3-isopropylprolyl-N-[5-chloro-2-(1H-1,2,4-triazol-1-yl)benzyl]-L-prolinamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1,2-Dichloroethane | HCID 11 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | HOAt | HCID 181649 | — |
| Reactant | 1-(tert-Butoxycarbonyl)-3-isopropyl-2-pyrrolidinecarboxylic acid | HCID 21866177 | — |
| Reactant | N-[5-chloro-2-(1H-1,2,4-triazol-1-yl)benzyl]-L-prolinamide | HCID 69656007 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 1-(tert-butoxycarbonyl)-3-isopropylprolyl-N-[5-chloro-2-(1H-1,2,4-triazol-1-yl)benzyl]-L-prolinamide | HCID 69655666 | — |
Reaction Steps
A mixture of 1-(tert-butoxycarbonyl)-3-isopropyl-dl-proline, (77 mg, 0.30 mmol), N-[5-chloro-2-(1H1,2,4-triazol-1-yl)benzyl]-L-prolinamide (Example 27, Step B, 113 mg, 0.30 mmol), HOAt (20 mg, 0.15 mmol), EDC (86 mg, 0.45 mmol) and Et3N (80 μL, 0.60 mmol) in 1.5 mL DMF was stirred at room temperature. The diastereomeric products were separated by reverse phase HPLC (30 min gradient elution with 95:5 H2O/0.1% TFA:CH3CN/0.1% TFA to 5:95 H2O/0.1% TFA:CH3CN/0.1% TFA) and carried on directly to deprotection.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07144899B2 |
| Source dataset | uspto-grants-2006_12 |
| ORD ID | ord-7c1061318f7b40258fe19787052f28e2 |
| Source note | uspto-grants-2006_12 |