HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethylamine → N2-(tert-butoxycarbonyl)-N,N,O-trimethyl-L-threoninamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethylamine | HCID 674 | — |
| 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 | (2S,3R)-2-{[(tert-butoxy)carbonyl]amino}-3-methoxybutanoic acid | HCID 15460346 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | N2-(tert-butoxycarbonyl)-N,N,O-trimethyl-L-threoninamide | HCID 86678875 | 77.7% |
Reaction Steps
To a solution of N-(tert-butoxycarbonyl)-O-methyl-L-threonine (2.33 g), 50% aqueous dimethylamine solution (1.08 g) and N-ethyl-N-(1-methylethyl)propan-2-amine (2.58 g) in DMF (30 mL) was added O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (4.18 g) under ice-cooling. The reaction mixture was stirred at room temperature overnight, the reaction mixture was added to water, and the mixture was extracted with ethyl acetate. The organic layer was separated, washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (2.02 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08772277B2 |
| Source dataset | uspto-grants-2014_07 |
| ORD ID | ord-8478cf14c7dd43728cab134aab6c8c2c |
| Source note | uspto-grants-2014_07 |