HuagongsheHuagongshe Chemistry Print Report · For research reference only
N-Methylbenzeneethanamine → [2-Methyl-1-(methyl-phenethyl-carbamoyl)-propyl]-carbamic acid tert-butyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | N-Methylbenzeneethanamine | HCID 11503 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Boc-DL-valine | HCID 270655 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 2733084 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | [2-Methyl-1-(methyl-phenethyl-carbamoyl)-propyl]-carbamic acid tert-butyl ester | HCID 67023731 | — |
Reaction Steps
A mixture of N-methyl-phenethyl-amine (2.2 mL, 15.3 mmol), 2-tert-butoxycarbonylamino-3-methyl-butyric acid (3.33 g, 15.3 mmol), HBTU (8.7 g, 22.95 mmol), DIPEA (6.1 mL, 33.7 mmol) and DMF (75 mL) was stirred at room temperature for 14 hours. To the resulting mixture was added sodium bicarbonate (400 mL) and the desired product was extracted with ethyl acetate (400 mL×2). The combined organic layers were washed with water, dried over MgSO4 and concentrated under reduced pressure to yield an oil. The oil was purified by column chromatography (50% EtOAc/heptane) to yield a residue.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07531545B2 |
| Source dataset | uspto-grants-2009_05 |
| ORD ID | ord-7c10d7dd65f843d0b5754a6184febf7c |
| Source note | uspto-grants-2009_05 |