HuagongsheHuagongshe Chemistry Print Report · For research reference only
2-Methoxybenzoic acid → Tert-Butyl 3-{[(2-methoxy benzoyl)amino]methyl}piperidine-1-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2-Methoxybenzoic acid | HCID 11370 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 1-Boc-3-(aminomethyl)piperidine | HCID 2756483 | — |
| 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 | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | Tert-Butyl 3-{[(2-methoxy benzoyl)amino]methyl}piperidine-1-carboxylate | HCID 86649438 | — |
Reaction Steps
HATU (293 mg, 0.77 mmol) was added to a DMF (3 mL) solution of the compound (150 mg, 0.7 mmol) synthesized in (2), 2-methoxybenzoic acid (117 mg, 0.77 mmol), and diisopropylethylamine (0.27 mL, 1.54 mmol), and the mixture was stirred at room temperature for 24 hours. After adding ethyl acetate, the reaction mixture was washed twice with distilled water, and once with saturated brine. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was then purified using silica gel column chromatography to obtain the target (244 mg, 100%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08188280B2 |
| Source dataset | uspto-grants-2012_05 |
| ORD ID | ord-843561ac40984701bf4901344069e4be |
| Source note | uspto-grants-2012_05 |