Imidazole → N-[5-((R)-2-Azido-1-triethylsilyloxyethyl)-2-benzyloxyphenyl]methanesulfonamide

HRID 2220652Notes

Reaction equation

HRID 2220652 reaction equation
N1C=CN=C1.[CH2:6]([Si:8](Cl)([CH2:11][CH3:12])[CH2:9][CH3:10])[CH3:7].[N:14]([CH2:17][C@@H:18]([C:20]1[CH:21]=[CH:22][C:23]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[C:24]([NH:26][S:27]([CH3:30])(=[O:29])=[O:28])[CH:25]=1)[OH:19])=[N+:15]=[N-:16].O>CN(C)C=O>[N:14]([CH2:17][C@@H:18]([C:20]1[CH:21]=[CH:22][C:23]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[C:24]([NH:26][S:27]([CH3:30])(=[O:28])=[O:29])[CH:25]=1)[O:19][Si:8]([CH2:11][CH3:12])([CH2:9][CH3:10])[CH2:6][CH3:7])=[N+:15]=[N-:16]

Participants

6

Reactant 4

HCID 795Imidazole2×HCID 962WaterHCID 13819Chlorotriethylsilane2×HCID 86611776N-[5-((R)-2-azido-1-hydroxyethyl)-2-benzyloxyphenyl]methanesulfonamide

Product 1

HCID 86611775N-[5-((R)-2-Azido-1-triethylsilyloxyethyl)-2-benzyloxyphenyl]methanesulfonamideYield 85.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Imidazole (0.46 g) and triethylsilyl chloride (0.82 g) were added to a solution of N-[5-((R)-2-azido-1-hydroxyethyl)-2-benzyloxyphenyl]methanesulfonamide (1.64 g) in N,N-dimethylformamide (20 mL), and the mixture was stirred at room temperature for 12 hrs. Imidazole (0.15 g) and triethylsilyl chloride (0.21 g) were added to the reaction mixture. After being stirred for additional 3 hrs, water was added to the mixture, and the resulting mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by medium-pressure silica gel column chromatography (eluent: n-hexane/ethyl acetate=5/1) to afford the title compound (1.84 g).

Workup

  1. stirringAfter being stirred for additional 3 hrs
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by medium-pressure silica gel column chromatography (eluent: n-hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-66c99e018df54774a978a365acd46240
Source dataset
uspto-grants-2008_08
Patent number
US07417169B2

Reaction notes

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