4-Toluenesulfonyl chloride → 3-({2-chloro-4-[(E)-2-cyclopentyl-1-(5-ethyl-6-methoxypyridin-2-yl)ethenyl]phenyl}sulfanyl)propyl 4-methylbenzenesulfonate

HRID 70593Notes

Reaction equation

HRID 70593 reaction equation
C(N(CC)CC)C.Cl.CN(C)C.[CH3:13][C:14]1[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:15]=1.[Cl:24][C:25]1[CH:30]=[C:29](/[C:31](/[C:38]2[CH:43]=[CH:42][C:41]([CH2:44][CH3:45])=[C:40]([O:46][CH3:47])[N:39]=2)=[CH:32]\[CH:33]2[CH2:37][CH2:36][CH2:35][CH2:34]2)[CH:28]=[CH:27][C:26]=1[S:48][CH2:49][CH2:50][CH2:51][OH:52]>C(Cl)(Cl)Cl.O>[CH3:13][C:14]1[CH:19]=[CH:18][C:17]([S:20]([O:52][CH2:51][CH2:50][CH2:49][S:48][C:26]2[CH:27]=[CH:28][C:29](/[C:31](/[C:38]3[CH:43]=[CH:42][C:41]([CH2:44][CH3:45])=[C:40]([O:46][CH3:47])[N:39]=3)=[CH:32]\[CH:33]3[CH2:37][CH2:36][CH2:35][CH2:34]3)=[CH:30][C:25]=2[Cl:24])(=[O:22])=[O:21])=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 10313079Trimethylamine HydrochlorideHCID 673999143-({2-chloro-4-[(E)-2-cyclopentyl-1-(5-ethyl-6-methoxypyridin-2-yl)ethenyl]phenyl}sulfanyl)propan-1-ol

Product 1

HCID 866580103-({2-chloro-4-[(E)-2-cyclopentyl-1-(5-ethyl-6-methoxypyridin-2-yl)ethenyl]phenyl}sulfanyl)propyl 4-methylbenzenesulfonateYield 93.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

Triethylamine (87 μL), trimethylamine hydrochloride (20 mg) and 4-methylbenzenesulfonyl chloride (60 mg) were sequentially added to a solution of 3-({2-chloro-4-[(E)-2-cyclopentyl-1-(5-ethyl-6-methoxypyridin-2-yl)ethenyl]phenyl}sulfanyl)propan-1-ol (95 mg) in chloroform (2 mL) under ice-cooling, and the mixture was stirred at room temperature for one hour. The reaction solution was poured into water, followed by extraction with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and filtered, after which the solvent was evaporated under reduced pressure to give 3-({2-chloro-4-[(E)-2-cyclopentyl-1-(5-ethyl-6-methoxypyridin-2-yl)ethenyl]phenyl}sulfanyl)propyl 4-methylbenzenesulfonate (120 mg) as a yellow amorphous.

Workup

  1. temperaturecooling
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customafter which the solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-742d30bd0979473baa9dfa3816a23980
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Reaction notes

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