Hydrochloric Acid → HCID 131722219, compound

HRID 1275174Notes

Reaction equation

HRID 1275174 reaction equation
[Si]([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:24]([C:27]2[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[C:29]([O:35][CH3:36])[CH:28]=2)(=[O:26])=[O:25])[CH2:12]1)(C(C)(C)C)(C)C.C(=O)([O-])O.[Na+].[CH3:42][S:43](Cl)(=[O:45])=[O:44].Cl>C(O)(=O)C.O1CCCC1.O.CN(C)C1C=CN=CC=1>[CH3:42][S:43]([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:24]([C:27]2[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[C:29]([O:35][CH3:36])[CH:28]=2)(=[O:26])=[O:25])[CH2:12]1)(=[O:45])=[O:44]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 131722217HCID 131722217, compound

Product 1

HCID 131722219HCID 131722219, compoundYield 89.1%

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

1.19 g (2.06 mmole) of 2-[(5R)-(3,4-dichlorophenyl)-3-(3,4-dimethoxybenzenesulfonyl)oxazolidin-5-yl]ethanol t-butyldimethylsilyl ether [prepared as described in step (a) above] were dissolved in 20 ml of a 3:3:1 by volume mixture of acetic acid, tetrahydrofuran and water, and the resulting mixture was then heated at 80° C. for 2 hours under a nitrogen atmosphere. At the end of this time, the reaction mixture was then neutralised with a saturated aqueous solution of sodium hydrogencarbonate and extracted with ethyl acetate. The organic extract was dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure, and the resulting residue was dissolved in 10 ml of pyridine. 23 mg (0.19 mmole) of 4-dimethylaminopyridine and 0.22 ml (2.84 mmole) of methanesulfonyl chloride were then added to the resulting solution, whilst ice-cooling. The mixture was then stirred for 2 hours at 0° C. under a nitrogen atmosphere. At the end of this time, the reaction mixture was poured into 200 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 2:1 to 1:2 by volume as the eluent, to give 992 mg of the title compound as white crystals.

Workup

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

Sources & evidence

ORD record
ord-0e0590142d1b4014930249ea37b850ac
Source dataset
uspto-grants-2000_12
Patent number
US06159967

Reaction notes

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