HuagongsheHuagongshe Chemistry Print Report · For research reference only
1-Hydroxybenzotriazole → ((S)-1-{2-[(S)-2-(2-Benzyl-2H-tetrazol-5-yl)-pyrrolidin-1-yl]-1-cyclohexyl-2-oxo-ethylcarbamoyl}-propyl)-methyl-carbamic acid tert-butyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 2733084 | — |
| Reactant | (2S)-2-(((1,1-Dimethylethoxy)carbonyl)methylamino)butanoic acid | HCID 15689337 | — |
| Reactant | 2-amino-1-[(2S)-2-(2-benzyltetrazol-5-yl)pyrrolidin-1-yl]-2-cyclohexylethanone;2,2,2-trifluoroacetic acid | HCID 86601084 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Dimethylacetamide | HCID 31374 | — |
| Product | ((S)-1-{2-[(S)-2-(2-Benzyl-2H-tetrazol-5-yl)-pyrrolidin-1-yl]-1-cyclohexyl-2-oxo-ethylcarbamoyl}-propyl)-methyl-carbamic acid tert-butyl ester | HCID 59788068 | — |
Reaction Steps
To a solution of (S)-2-(tert-butoxycarbonyl-methyl-amino)-butyric acid (53.0 mg, 0.24 mmol) in DMA (2 mL) is added HBTU (125.0 mg, 0.33 mmol), HOBt (44.6 mg, 0.33 mmol) and diisopropylethylamine (192 uL, 1.1 mmol). The mixture is stirred at room temperature for 5 minutes. A solution of compound F in DCM (2 mL) is added to the above mixture at 0° C. The reaction mixture is stirred at room temperature for 1 hour and concentrated under vacuum. The residue is diluted with EtOAc. The organic is washed with brine, citric acid (5%), brine, NaHCO3(Sat.) and brine. The organic layer is then dried and concentrated under vacuum. The crude oil is used directly in the next step without further purification. M+H+=554.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08338440B2 |
| Source dataset | uspto-grants-2012_12 |
| ORD ID | ord-c7f05225e96248519b5c3dcd65489bca |
| Source note | uspto-grants-2012_12 |