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2-Pyridinecarboxamide → N-(3-hydroxy-4-methoxy-2-pyridylcarbonyl)-2-amino-2-deoxy-alpha-D-glucopyranose
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | 2-Pyridinecarboxamide | HCID 15070 | — |
| 反応物 | Lithium hydroxide, monohydrate | HCID 168937 | — |
| 反応物 | 3-Hydroxy-4-methoxypyridine-2-carboxylic acid | HCID 11041121 | — |
| 反応物 | [(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 | — |
| 溶媒 | Methanol | HCID 887 | — |
| 生成物 | N-(3-hydroxy-4-methoxy-2-pyridylcarbonyl)-2-amino-2-deoxy-alpha-D-glucopyranose | HCID 18681678 | 88% |
反応手順
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%).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US06355660B1 |
| 出典データセット | uspto-grants-2002_03 |
| ORD ID | ord-1aeb1dca29584c1cbe1ed19262d06b97 |
| 出典メモ | uspto-grants-2002_03 |