HuagongsheHuagongshe Chemistry Print Report · For research reference only
2-Pyridinecarboxamide → N-(3-hydroxy-4-methoxy-2-pyridylcarbonyl)-2-amino-2-deoxy-alpha-D-glucopyranose
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2-Pyridinecarboxamide | HCID 15070 | — |
| Reactant | Lithium hydroxide, monohydrate | HCID 168937 | — |
| Reactant | 3-Hydroxy-4-methoxypyridine-2-carboxylic acid | HCID 11041121 | — |
| Reactant | [(3S,7R,8R,9S)-7-benzyl-8-hydroxy-9-methyl-2,6-dioxo-[1,5]dioxonane-3-yl]-carbamic acid tert-butyl ester | HCID 69151164 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | N-(3-hydroxy-4-methoxy-2-pyridylcarbonyl)-2-amino-2-deoxy-alpha-D-glucopyranose | HCID 18681678 | 88% |
Reaction Steps
1,3,4,6-Tetra-O-acetyl-2-amino-2-deoxy-alpha-D-glucopyranose (151) and 3-hydroxy-4-methoxypicolinic acid were coupled together using standard coupling procedure C. To a solution of the resulting picolinamide (0.19 g, 0.38 mmol) in 6 mL of methanol was added lithium hydroxide monohydrate (0.92 mmol, 40 mg). The reaction mixture was stirred at room temperature overnight. The solution was neutralized by the addition of DOWEX® 5×8-100 acidic resin (0.5 g). The mixture was filtered and concentrated to afford the title compound (110 mg, 88%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06706740B2 |
| Source dataset | uspto-grants-2004_03 |
| ORD ID | ord-d6fa8b29480741348e488d2b098d95b7 |
| Source note | uspto-grants-2004_03 |