Hydrochloric Acid → HCID 131722207, compound

HRID 1275158Notes

Reaction equation

HRID 1275158 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]([C:24](=[O:37])[C:25]2[CH:30]=[C:29]([O:31][CH3:32])[C:28]([O:33][CH3:34])=[C:27]([O:35][CH3:36])[CH:26]=2)[CH2:12]1)(C(C)(C)C)(C)C.C(=O)([O-])O.[Na+].[CH3:43][S:44](Cl)(=[O:46])=[O:45].Cl>C(O)(=O)C.O1CCCC1.O.CN(C)C1C=CN=CC=1.C(OCC)(=O)C.CCCCCC>[CH3:43][S:44]([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]([C:24](=[O:37])[C:25]2[CH:30]=[C:29]([O:31][CH3:32])[C:28]([O:33][CH3:34])=[C:27]([O:35][CH3:36])[CH:26]=2)[CH2:12]1)(=[O:46])=[O:45]

Participants

11

Reactant 4

HCID 313Hydrochloric AcidHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 131722208HCID 131722208, compound

Product 1

HCID 131722207HCID 131722207, compoundYield 82%

Reagents, catalysts & solvents 6

HCID 142844-(Dimethylamino)pyridineCatalystHCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

3.95 g (6.92 mmole) of 2-[(5R)-(3,4-dichlorophenyl)-3-(3,4,5-trimethoxybenzoyl)oxazolidin-5-yl]ethanol t-butyldimethylsilyl ether [prepared as described in step (f) above] were dissolved in 70 ml of a 3:3:1 by volume mixture of acetic acid, tetrahydrofuran and water. The mixture was then heated under a nitrogen atmosphere at 80° C. for 8 hours. At the end of this time, the solution was neutralised by the addition of a saturated aqueous solution of sodium hydrogencarbonate and extracted with ethyl acetate. The organic layer was then dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure, and the resulting residue was dissolved in 30 ml of pyridine. 70 mg (0.57 mmole) of 4-dimethylaminopyridine and 0.66 ml (8.53 mmole) of methanesulfonyl chloride were added, whilst ice-cooling, to the resulting solution, and the mixture was then stirred under a nitrogen atmosphere at 0° C. for 2 hours. 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 three times, each time with 100 ml of ethyl acetate. The combined organic extracts were 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 flash column chromatography, using a gradient elution method, with mixtures of hexane and ethyl acetate ranging from 5:1 to 1:1 by volume as the eluent, to obtain 3.02 g (yield 82%) of the title compound as a white amorphous substance.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was then dried over anhydrous magnesium sulfate
  3. customThe solvent was removed by distillation under reduced pressure
  4. dissolutionthe resulting residue was dissolved in 30 ml of pyridine
  5. temperaturecooling, to the resulting solution
  6. temperaturecooled 10%
  7. extractionextracted three times
  8. washThe combined organic extracts were washed with a saturated aqueous solution of sodium chloride
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customThe solvent was removed by distillation under reduced pressure
  11. customthe resulting residue was purified by silica gel flash column chromatography
  12. washa gradient elution method

Sources & evidence

ORD record
ord-1fa9e28697064aea880c4715d8a1269b
Source dataset
uspto-grants-2000_12
Patent number
US06159967

Reaction notes

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