Hydrochloric Acid → HCID 131722215, compound

HRID 1279359Notes

Reaction equation

HRID 1279359 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[C@@H:14]([CH2:15][CH2:16][OH:17])[O:13][CH2:12][CH2:11][N:10]2[C:18](=[O:30])[CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH:27]([CH3:29])[CH3:28])[CH:21]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].[CH3:31][S:32](Cl)(=[O:34])=[O:33].Cl>N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[CH3:31][S:32]([O:17][CH2:16][CH2:15][C@H:14]1[O:13][CH2:12][CH2:11][N:10]([C:18](=[O:30])[CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH:27]([CH3:28])[CH3:29])[CH:21]=2)[CH:9]1[C:4]1[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=1)(=[O:34])=[O:33]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 31297Methanesulfonyl chlorideHCID 131722214HCID 131722214, compound

Product 1

HCID 131722215HCID 131722215, compoundYield 94.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

1.81 g (4.00 mmole) of 2-{(2R)-(3,4-dichlorophenyl)-4-[(3-isopropoxyphenyl)acetyl]morpholin-2-yl}ethanol [prepared as described in step (a) above] were dissolved in 5 ml of pyridine, and 45 mg (0.40 mmole) of 4-dimethylaminopyridine and 0.46 ml (6.00 mmole) of methanesulfonyl chloride were added to the resulting solution, whilst ice-cooling. The mixture was then stirred at 0° C. for 2 hours under a nitrogen atmosphere. At the end of this time, the reaction mixture was poured into 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 1:1 to 1:2 by volume as the eluent, to give 2.00 g of the title compound as a colorless oil.

Workup

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

Sources & evidence

ORD record
ord-ee165280de724ac38403588dc094b934
Source dataset
uspto-grants-2002_09
Patent number
US06448247B1

Reaction notes

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