Trimethylsilyl iodide → HCID 58503923, compound

HRID 2407790Notes

Reaction equation

HRID 2407790 reaction equation
C(OC([NH:11][CH2:12][CH2:13][CH2:14][N:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:18](=[O:25])[C:17]([CH2:26][CH:27]2[CH2:32][CH2:31][N:30]([CH2:33][C:34]3[S:38][C:37]([C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][N:40]=4)=[N:36][CH:35]=3)[CH2:29][CH2:28]2)=[C:16]1[C:45]([O:47][CH3:48])=[O:46])=O)C1C=CC=CC=1.I[Si](C)(C)C>C(#N)C.C(OCC)(=O)C>[NH2:11][CH2:12][CH2:13][CH2:14][N:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:18](=[O:25])[C:17]([CH2:26][CH:27]2[CH2:32][CH2:31][N:30]([CH2:33][C:34]3[S:38][C:37]([C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][N:40]=4)=[N:36][CH:35]=3)[CH2:29][CH2:28]2)=[C:16]1[C:45]([O:47][CH3:48])=[O:46]

Participants

5

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 58503956HCID 58503956, compound

Product 1

HCID 58503923HCID 58503923, compoundYield 16.9%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of the compound prepared in Example 330 (37 mg) in acetonitrile (1 mL) was treated with iodotrimethylsilane (0.015 mL) for 30 minutes at room temperature. The solution was diluted with ethyl acetate, washed with saturated aqueous sodium bicarbonate solution and brine. The organics were dried over magnesium sulfate, filtered and concentrated under reduced pressure to afford the crude material, which was purified by preparative thin layer chromatography (eluant: 20% (9:1 methanol/concentrated ammonium hydroxide)/ethyl acetate) to furnish the title compound (5 mg) with the following physical properties.

Workup

  1. washwashed with saturated aqueous sodium bicarbonate solution and brine
  2. dry with materialThe organics were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customto afford the crude material, which
  6. customwas purified by preparative thin layer chromatography (eluant: 20% (9:1 methanol/concentrated ammonium hydroxide)/ethyl acetate)

Sources & evidence

ORD record
ord-2a2bebbdf526404a818eada4d709b133
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

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