HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → Boc-L-Ile-DL-Pip-OBzl
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | tert-Butoxycarbonyl-L-isoleucine | HCID 2724762 | — |
| 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 | Benzyl piperidine-2-carboxylate hydrochloride | HCID 66751062 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | Boc-L-Ile-DL-Pip-OBzl | HCID 131724669 | 115% |
Reaction Steps
Boc-L-Ile-OH ½ H2O (3.92 g, 16.8 mmol), H-D,L-Pip-OBzl HCl (3.57 g, 12 mmol) and HATU (7.75 g, 18 mmol) were dissolved in DMF (15 ml), mixed with Et3N (4.76 ml, 30 mmol) under ice cooling, and then stirred overnight. The reaction mixture was concentrated, extracted with ethyl acetate (120 ml), and washed twice with 10% citric acid, 4% NaHCO3 and then brine, respectively. After drying over magnesium sulfate, ethyl acetate was distilled off. The residue was vacuum dried and purified by flash chromatography (3.5×20 cm) with CHCl3/MeOH (99:1) to yield Boc-L-Ile-D,L-Pip-OBzl (5.90 g, 13.8 mmol; yield 97%) as an oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06825317B2 |
| Source dataset | uspto-grants-2004_11 |
| ORD ID | ord-befb98a70aa1425eb3db42fadc161014 |
| Source note | uspto-grants-2004_11 |