Water → HCID 66858363, compound

HRID 1888325Notes

Reaction equation

HRID 1888325 reaction equation
[Si:1]([O:8][CH2:9][C@H:10]1[CH2:14][CH2:13][C:12](=[O:15])[N:11]1[CH2:16][C:17]1[S:18][CH:19]=[C:20](/[CH:22]=[CH:23]/[C:24]([OH:26])=[O:25])[N:21]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH2:27](I)[CH2:28][CH2:29][CH3:30].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[Si:1]([O:8][CH2:9][C@H:10]1[CH2:14][CH2:13][C:12](=[O:15])[N:11]1[CH2:16][C:17]1[S:18][CH:19]=[C:20](/[CH:22]=[CH:23]/[C:24]([O:26][CH2:27][CH2:28][CH2:29][CH3:30])=[O:25])[N:21]=1)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 10962Butyl iodideHCID 11430Potassium CarbonateHCID 66858048HCID 66858048, compound

Product 1

HCID 66858363HCID 66858363, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the compound 72 (980 mg) in dimethylformamide (3.00 mL) was added n-butyl iodide (570 μL) at room temperature and then thereto was added potassium carbonate (691 mg) at 0° C. The solution was stirred at room temperature overnight. Water was added to the reaction solution, which was extracted with ethyl acetate. The organic layer was washed water and brine, dried over anhydrous sodium sulfate and concentrated. The organic residue was purified by column chromatography on silica gel (n-hexane:ethyl acetate=78:22→50:50) to give the title compound (960 mg) having the following physical data.

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe organic layer was washed water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe organic residue was purified by column chromatography on silica gel (n-hexane:ethyl acetate=78:22→50:50)

Sources & evidence

ORD record
ord-f7b71c666047434abbdd8d4eb29baa23
Source dataset
uspto-grants-2013_08
Patent number
US08501793B2

Reaction notes

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