Water → HCID 22995917, compound

HRID 1167195Notes

Reaction equation

HRID 1167195 reaction equation
[CH2:1]([N:3](CC)[CH2:4][CH3:5])[CH3:2].CS(Cl)(=O)=O.[F:13][C:14]([F:41])([F:40])[S:15]([O:18][C:19]1[CH:28]=[CH:27][C:26]2[C:21](=[C:22]([CH:29](O)[CH2:30][O:31][Si:32]([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:34])[CH3:33])[CH:23]=[CH:24][CH:25]=2)[N:20]=1)(=[O:17])=[O:16].O>C(OCC)C>[F:41][C:14]([F:40])([F:13])[S:15]([O:18][C:19]1[CH:28]=[CH:27][C:26]2[C:21](=[C:22]([CH:29]([N:3]([CH2:4][CH3:5])[CH2:1][CH3:2])[CH2:30][O:31][Si:32]([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:33])[CH3:34])[CH:23]=[CH:24][CH:25]=2)[N:20]=1)(=[O:17])=[O:16]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 22995910HCID 22995910, compound

Product 1

HCID 22995917HCID 22995917, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

13.21 ml of triethylamine and 7 ml of methanesulfonyl chloride are successively added to a solution, cooled to 0° C. with an ice bath, of 13.8 g (30.53 mmol) of 2-trifluoromethanesulfonyloxy-8-(1′-hydroxy-2′-tert-butyldimethylsilyloxyethyl)quinoline in 300 ml of ethyl ether. The mixture is stirred for 30 min at 0° C. and then for 10 min at ambient temperature and is hydrolyzed by the addition of 300 ml of water. Extraction is carried out with ethyl acetate (3×250 ml). The organic phases are combined, dried over magnesium sulfate, filtered and concentrated under vacuum. The residue is dissolved in 200 ml of chloroform and 45 ml of diethylamine and the mixture is brought to reflux for 16 h. 200 ml of water are added and extraction is carried out with ethyl acetate (3×150 ml). The organic phases are combined, dried over magnesium sulfate, filtered and concentrated under vacuum. The residue is purified by silica chromatographic column (eluent: cyclohexane/ethyl acetate 8/2) to provide 14 g of 2-trifluoromethane sulfonyloxy-8-(1-diethylamino-2-tert-butyldimethylsilyloxyethyl)quinoline in the form of a yellow oil. (Yield: 90%)

Workup

  1. waitfor 10 min at ambient temperature
  2. extractionExtraction
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. dissolutionThe residue is dissolved in 200 ml of chloroform
  7. temperatureto reflux for 16 h
  8. addition200 ml of water are added
  9. extractionextraction
  10. dry with materialdried over magnesium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated under vacuum
  13. customThe residue is purified by silica chromatographic column (eluent: cyclohexane/ethyl acetate 8/2)

Sources & evidence

ORD record
ord-ee6d6e6b780e412a90a22285fa4379bb
Source dataset
uspto-grants-2003_09
Patent number
US06617336B1

Reaction notes

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