Hydrochloric Acid → HCID 131722217, compound

HRID 1275173Notes

Reaction equation

HRID 1275173 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][C@H:11]1[O:15][CH:14]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([Cl:23])[CH:17]=2)[NH:13][CH2:12]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH3:24][O:25][C:26]1[CH:27]=[C:28]([S:34](Cl)(=[O:36])=[O:35])[CH:29]=[CH:30][C:31]=1[O:32][CH3:33].Cl>N1C=CC=CC=1>[Si:1]([O:8][CH2:9][CH2:10][C@H:11]1[O:15][CH:14]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([Cl:23])[CH:17]=2)[N:13]([S:34]([C:28]2[CH:29]=[CH:30][C:31]([O:32][CH3:33])=[C:26]([O:25][CH3:24])[CH:27]=2)(=[O:36])=[O:35])[CH2:12]1)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 27341833,4-Dimethoxybenzenesulfonyl chlorideHCID 131722218HCID 131722218, compound

Product 1

HCID 131722217HCID 131722217, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1.00 g (2.72 mmole) of 2-[(5R)-(3,4-dichlorophenyl)oxazolidin-5-yl]ethanol t-butyldimethylsilyl ether [prepared as described in the first part of Example 1(f)] was dissolved in 10 ml of pyridine, and 773 mg (3.27 mmole) of 3,4-dimethoxybenzenesulfonyl chloride were added to the resulting solution, whilst ice-cooling. The mixture was then stirred for 2 hours under a nitrogen atmosphere. At the end of this time, the reaction mixture was poured into 100 ml of ice-cooled 10% w/v aqueous hydrochloric acid, and then extracted with ethyl acetate. The organic extract was washed with a saturated aqueous solution of sodium chloride and then dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure, and the resulting residue was purified by silica gel column chromatography, using a gradient elution method, with mixtures of hexane and ethyl acetate ranging from 10:1 to 2:1 by volume as the eluent, to give 1.27 g of the title compound as white crystals.

Workup

  1. temperaturecooling
  2. temperaturecooled 10%
  3. extractionextracted with ethyl acetate
  4. extractionThe organic extract
  5. washwas washed with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was removed by distillation under reduced pressure
  8. customthe resulting residue was purified by silica gel column chromatography
  9. washa gradient elution method

Sources & evidence

ORD record
ord-e0ee80a7309f463e90687d23e70449dd
Source dataset
uspto-grants-2000_12
Patent number
US06159967

Reaction notes

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