Sodium Iodide → ({2-[({(3S,7R,8R,9S)-7-benzyl-8-(hydroxy)-9-methyl-2,6-dioxo-1,5-dioxonan-3-yl}amino)carbonyl]-4-methoxypyridine-3-yl}oxy)methyl acetate

HRID 1071008ノート

反応式

HRID 1071008 の反応式
[CH2:1]([C@@H:8]1[C@@H:16]([OH:17])[C@H:15]([CH3:18])[O:14][C:13](=[O:19])[C@@H:12]([NH:20][C:21]([C:23]2[C:28]([OH:29])=[C:27]([O:30][CH3:31])[CH:26]=[CH:25][N:24]=2)=[O:22])[CH2:11][O:10][C:9]1=[O:32])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].[C:41]([O:44][CH2:45]Br)(=[O:43])[CH3:42]>CC(C)=O.C(OCC)(=O)C.O>[C:41]([O:44][CH2:45][O:29][C:28]1[C:23]([C:21]([NH:20][C@H:12]2[CH2:11][O:10][C:9](=[O:32])[C@H:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[C@@H:16]([OH:17])[C@H:15]([CH3:18])[O:14][C:13]2=[O:19])=[O:22])=[N:24][CH:25]=[CH:26][C:27]=1[O:30][CH3:31])(=[O:43])[CH3:42]

参加物

8

反応物 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 68536Bromomethyl acetateHCID 11236123N-((3S,7R,8R,9S)-7-benzyl-8-hydroxy-9-methyl-2,6-dioxo-1,5-dioxonan-3-yl)-3-hydroxy-4-methoxypicolinamide

生成物 1

HCID 69801412({2-[({(3S,7R,8R,9S)-7-benzyl-8-(hydroxy)-9-methyl-2,6-dioxo-1,5-dioxonan-3-yl}amino)carbonyl]-4-methoxypyridine-3-yl}oxy)methyl acetate収率 90.3%

試薬・触媒・溶媒 3

HCID 180Acetone溶媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
2.5 °C

実験手順

To a solution of Compound 1 (40 g, 90.09 mmol) in dry acetone (360 mL) was added powdered potassium carbonate (14.92 g, 108 mmol) in three portions over 5 min, the mixture stirred at 0-5° C. for 20 min and sodium iodide (2.697 g, 18 mmol) was added. Bromomethyl acetate (16.54 g, 108.11 mmol) was then added dropwise over 15 min using an addition funnel, the mixture stirred at 0-5° C. for 1 h then at RT for 3 hours. The mixture was diluted with ethyl acetate (700 mL) and water (200 mL), the organic phase rinsed with water (×2), brine. (×2), dried over sodium sulfate and concentrated in vacuo to give a solid, which was passed through silica gel (1:1 hexanes/acetone) to give 42 g of Compound 3. (M+1)+=517. Spectral data were consistent with the assigned structure.

後処理

  1. stirringthe mixture stirred at 0-5° C. for 1 h
  2. waitat RT for 3 hours
  3. washthe organic phase rinsed with water (×2), brine
  4. dry with material(×2), dried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customto give a solid, which

出典と根拠

ORDレコード
ord-d65fa5081ff9466e9a73dc6efadf6ea2
出典データセット
uspto-grants-2005_06
特許番号
US06903219B2

反応ノート

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