Hydrochloric Acid → HCID 131722847, compound

HRID 1596090Notes

Reaction equation

HRID 1596090 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[Cl:6][C:7]1[CH:8]=[C:9]([CH:14]2[C@@H:19]([CH2:20][CH2:21][OH:22])[O:18][CH2:17][CH2:16][N:15]2[C:23]([CH:25]2[CH2:28][CH2:27][CH2:26]2)=[O:24])[CH:10]=[CH:11][C:12]=1[Cl:13].Cl>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[CH3:1][S:2]([O:22][CH2:21][CH2:20][C@H:19]1[O:18][CH2:17][CH2:16][N:15]([C:23]([CH:25]2[CH2:26][CH2:27][CH2:28]2)=[O:24])[CH:14]1[C:9]1[CH:10]=[CH:11][C:12]([Cl:13])=[C:7]([Cl:6])[CH:8]=1)(=[O:4])=[O:3]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 31297Methanesulfonyl chlorideHCID 131722848HCID 131722848, compound

Product 1

HCID 131722847HCID 131722847, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

Methanesulfonyl chloride (0.071 ml, 0.92 mmol) and 4-dimethylaminopyridine (catalytic amount) were added to a solution of 2-[(2R)-(3,4-dichlorophenyl)-4-(cyclobutanecarbonyl)morpholin-2-yl]ethanol (219 mg, 0.61 mmol), which was prepared in Example 1(a), in pyridine (2 ml) with ice-cooling under a nitrogen atmosphere. The mixture was stirred at the same temperature for 30 minutes. The reaction mixture was acidified with ice-cooled hydrochloric acid (10%) and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The ethyl acetate was distilled off under reduced pressure. The residue was purified by silica gel thin layer chromatography using n-hexane/ethyl acetate=¼ as a developing solvent to afford the desired compound (255 mg, 96%) as a white amorphous solid.

Workup

  1. temperaturecooling under a nitrogen atmosphere
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe ethyl acetate was distilled off under reduced pressure
  6. customThe residue was purified by silica gel thin layer chromatography

Sources & evidence

ORD record
ord-4457872cf7e34824a36fe7daf3ea46b1
Source dataset
uspto-grants-2001_09
Patent number
US06288059B1

Reaction notes

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