Imidazole → HCID 22710932, compound

HRID 352836Notes

Reaction equation

HRID 352836 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([S:14]([C:17]2[CH:26]=[CH:25][C:24]3[C:19](=[CH:20][CH:21]=[C:22]([Cl:27])[CH:23]=3)[CH:18]=2)(=[O:16])=[O:15])[CH2:10][CH:9]1[CH2:28][CH2:29][OH:30])=[O:7])([CH3:4])([CH3:3])[CH3:2].N1C=CN=C1.[C:36]([Si:40](Cl)([C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)([CH3:39])([CH3:38])[CH3:37]>CN(C)C=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([S:14]([C:17]2[CH:26]=[CH:25][C:24]3[C:19](=[CH:20][CH:21]=[C:22]([Cl:27])[CH:23]=3)[CH:18]=2)(=[O:15])=[O:16])[CH2:10][CH:9]1[CH2:28][CH2:29][O:30][Si:40]([C:36]([CH3:39])([CH3:38])[CH3:37])([C:47]1[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=1)[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 22709724HCID 22709724, compound

Product 1

HCID 22710932HCID 22710932, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In N,N-dimethylformamide (15 ml) was dissolved 1-tert-butoxycarbonyl-4-[(6-chloronaphthalen-2-yl)sulfonyl]-2-(2-hydroxyethyl)piperazine (739 mg) and imidazole (226 mg). Under ice cooling, tert-butylchlorodiphenylsilane (0.70 ml) was added to the resulting solution, followed by stirring at room temperature for 23 hours. The reaction mixture was distilled off under reduced pressure. The residue was extracted with methylene chloride and a saturated aqueous solution of sodium bicarbonate. The organic layer thus obtained was washed with dilute hydrochloric acid and saturated aqueous NaCl solution, dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent. The residue was purified by column chromatography (hexane:ethyl acetate=2:1˜:2) using as a carrier silica gel, whereby the title compound (804 mg) was obtained as a pale yellow oil.

Workup

  1. distillationThe reaction mixture was distilled off under reduced pressure
  2. extractionThe residue was extracted with methylene chloride
  3. customThe organic layer thus obtained
  4. washwas washed with dilute hydrochloric acid and saturated aqueous NaCl solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationdistilled under reduced pressure
  7. customto remove the solvent
  8. customThe residue was purified by column chromatography (hexane:ethyl acetate=2:1˜:2)
  9. customwas obtained as a pale yellow oil

Sources & evidence

ORD record
ord-a3f34bd8b2b14dc28e7c2be642f55b44
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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