Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 2733084 | — |
| Reactant | methyl (2S)-2-amino-3-{[(tert-butoxy)carbonyl]amino}propanoate hydrochloride | HCID 18334328 | — |
| Reactant | 2-[(tert-Butoxycarbonyl)amino]-4-(trifluoromethyl)-1,3-thiazole-5-carboxylic acid | HCID 53423479 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 88898037 | HCID 88898037 | 78.2% |
Reaction Steps
To a solution of 2-tert-Butoxycarbonylamino-4-trifluoromethyl-thiazole-5-carboxylic acid (6.23 g, 19.96) in anhydrous DMF (100 mL) was added HBTU (8.29 g, 24.97 mmol), HOBt (3.39 g, 19.96 mmol), H-DAP(BOC)-OME HCL (8.08 g, 31.02 mmol) and triethylamine (11.97 mL, 85.94 mmol). The reaction mixture was stirred at 25′C for 1 h and concentrated under reduced pressure to remove most of the DMF. The residue was diluted with ethyl acetate (200 mL), washed with 1:1 water/brine (40 mL), aqueous 1N HCl (40 mL), brine (40 mL), dried over MgSO4, filtered and concentrated under reduced pressure. The resulting crude compound was purified by flash chromatography (40% to 100% EtOAc in hexanes) to give (S)-3-tert-Butoxycarbonylamino-2-[(2-tert-butoxycarbonylamino-4-trifluoromethyl-thiazole-5-carbonyl)-amino]-propionic acid methyl ester (8 g, 78%) as a pale yellow foam. MS m/e 513.5 (M+H+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08404859B2 |
|---|
| Source dataset | uspto-grants-2013_03 |
|---|
| ORD ID | ord-1651e58596c14467896095ec75ae2d8e |
|---|
| Source note | uspto-grants-2013_03 |
|---|
