HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ammonium Chloride → (2S)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-4-(2-amino-2-oxoethyl)-2-carbamoyl-5,6-dihydropyridine-1(2H)-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ammonium Chloride | HCID 25517 | — |
| 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)-5-(N-(allyloxy)-2-nitrophenylsulfonamido)-4-(2-amino-2-oxoethyl)-1-(tert-butoxycarbonyl)-1,2,5,6-tetrahydropyridine-2-carboxylic acid | HCID 89851815 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | (2S)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-4-(2-amino-2-oxoethyl)-2-carbamoyl-5,6-dihydropyridine-1(2H)-carboxylate | HCID 89852287 | — |
Reaction Steps
To a stirred solution of (2S)-5-(N-(allyloxy)-2-nitrophenylsulfonamido)-4-(2-amino-2-oxoethyl)-1-(tert-butoxycarbonyl)-1,2,5,6-tetrahydropyridine-2-carboxylic acid (crude, 2.79 g, 5.16 mmol), ammonium chloride (552 mg, 10.32 mmol), HATU (3.93 g, 10.32 mmol) in DMF (20 mL) at 0° C., was added DIPEA (2.67 g, 20.65 mmol). After stirring at room temperature for 1 hr, 50 mL EtOAc and 50 mL water was added. The organic layer was washed with water, brine and dried over MgSO4, filtered and concentrated to give a residue, which was purified on silica gel column eluting with 0-100% ethyl acetate/hexanes to afford an off-white solid, 1.36 g, 49%.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09309245B2 |
| Source dataset | uspto-grants-2016_04 |
| ORD ID | ord-ebe5fcb60a0a422f875c36ae8e94f2f0 |
| Source note | uspto-grants-2016_04 |