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 1071008Notes

Reaction equation

HRID 1071008 reaction equation
[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]

Participants

8

Reactant 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

Product 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 acetateYield 90.3%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
2.5 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-d65fa5081ff9466e9a73dc6efadf6ea2
Source dataset
uspto-grants-2005_06
Patent number
US06903219B2

Reaction notes

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