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 1071008노트

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HRID 1071008 반응식
[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]

참가 물질

8

반응물 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

생성물 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 acetate수율 90.3%

시약·촉매·용매 3

HCID 180Acetone용매HCID 962Water용매HCID 8857Ethyl Acetate용매

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온도
2.5 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-d65fa5081ff9466e9a73dc6efadf6ea2
출처 데이터셋
uspto-grants-2005_06
특허 번호
US06903219B2

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