2-Pyridinecarboxamide → N-(3-hydroxy-4-methoxy-2-pyridylcarbonyl)-2-amino-2-deoxy-alpha-D-glucopyranose

HRID 277164

反応式

HRID 277164 の反応式
C(O[C:6](=[O:28])[NH:7][C@H:8]1[CH2:16][O:15]C(=O)[C@H](CC2C=CC=CC=2)[C@@H:12]([OH:25])[C@H:11]([CH3:26])[O:10][C:9]1=[O:27])(C)(C)C.[OH:29][C:30]1[C:31](C(O)=O)=[N:32][CH:33]=[CH:34][C:35]=1[O:36][CH3:37].N1C=CC=CC=1C(N)=[O:48].O.[OH-].[Li+]>CO>[OH:29][C:30]1[C:31]([C:6]([NH:7][C@@H:8]2[C@@H:16]([OH:15])[C@H:26]([OH:48])[C@@H:11]([CH2:12][OH:25])[O:10][C@@H:9]2[OH:27])=[O:28])=[N:32][CH:33]=[CH:34][C:35]=1[O:36][CH3:37]

参加物

6

反応物 4

HCID 150702-PyridinecarboxamideHCID 168937Lithium hydroxide, monohydrateHCID 110411213-Hydroxy-4-methoxypyridine-2-carboxylic acidHCID 69151164[(3S,7R,8R,9S)-7-benzyl-8-hydroxy-9-methyl-2,6-dioxo-[1,5]dioxonane-3-yl]-carbamic acid tert-butyl ester

生成物 1

HCID 18681678N-(3-hydroxy-4-methoxy-2-pyridylcarbonyl)-2-amino-2-deoxy-alpha-D-glucopyranose収率 88%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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%).

後処理

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated

出典と根拠

ORDレコード
ord-1aeb1dca29584c1cbe1ed19262d06b97
出典データセット
uspto-grants-2002_03
特許番号
US06355660B1

関連ノート

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