Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Reactant | (2R,3R)-3-amino-2-hydroxy-4-(2-trifluoromethyl-phenyl)-butyric acid ethyl ester | HCID 71073550 | — |
| Reactant | 1-(4-Methoxybenzyl)-1H-pyrazole-3,5-dicarboxylic Acid | HCID 71074119 | — |
| Solvent | Acetic Acid | HCID 176 | — |
| Solvent | Ethanol | HCID 702 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | Trifluoroacetic acid | HCID 6422 | 95% |
| Product | 5-[(1R,2R)-2-Carboxy-2-hydroxy-1-(2-trifluoromethylbenzyl)-ethylcarbamoyl]-2-(4-methoxybenzyl)-2H-pyrazole-3-carboxylic Acid | HCID 71074141 | — |
Reaction Steps
1-(4-Methoxybenzyl)-1H-pyrazole-3,5-dicarboxylic acid (63.8 mg, 231 μmol, 1.0 eq.), HATU (88 mg, 230 μmol, 1.0 eq.), and (2R,3R)-3-amino-2-hydroxy-4-(2-trifluoromethyl-phenyl)-butyric acid ethyl ester (67.3 mg, 231 μmol, 1.0 eq.) were dissolved in DMF (5 mL) and stirred at room temperature for 2 minutes. DIPEA (121 μL, 3.0 eq.) was added and the mixture was stirred for 1 hour. The crude material was then dissolved in EtOH, and enough equivalents of 10N NaOH were added to make the solution basic. The reaction was monitored for 1 hour until completion. The solution was re-acidified with an equal volume of AcOH and vacuumed to dryness. The product was purified by preparative HPLC to yield the title compound as a TFA salt (12 mg, 95% purity). MS m/z [M+H]+ calc'd for C24H22F3N3O7, 522.14. found 522.2.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09422245B2 |
|---|
| Source dataset | uspto-grants-2016_08 |
|---|
| ORD ID | ord-60f0365392fe464dbe5c12297edc5f47 |
|---|
| Source note | uspto-grants-2016_08 |
|---|
