Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethylamine | HCID 674 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | N-(Benzyloxycarbonyl)aspartic acid | HCID 2723942 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 71247139 | HCID 71247139 | 21.5% |
Reaction Steps
To a solution of 50% aqueous dimethylamine solution (2.16 g) and N-[(benzyloxy)carbonyl]-L-aspartic acid (2.13 g) and N-ethyl-N-(1-methylethyl)propan-2-amine (4.12 g) in DMF (20 mL) was added O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (6.06 g) at room temperature. The reaction mixture was stirred at room temperature overnight. Water was added to the reaction mixture at room temperature, 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 (NH, methanol/ethyl acetate) to give the title compound (550 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08772277B2 |
|---|
| Source dataset | uspto-grants-2014_07 |
|---|
| ORD ID | ord-70b330f016d8497eb82835c60de45637 |
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| Source note | uspto-grants-2014_07 |
|---|
