Pyridine → N-allyltaurine isopropyl ester

HRID 587989Notes

Reaction equation

HRID 587989 reaction equation
ClCC[S:4](Cl)(=[O:6])=[O:5].[N:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Cl.C(N)C=C.C(N(C(C)C)CC)(C)C.[CH3:28][CH:29]([OH:31])[CH3:30]>>[CH:29]([O:31][S:4](=[O:5])(=[O:6])[CH2:12][CH2:13][NH:8][CH2:9][CH:10]=[CH2:11])([CH3:30])[CH3:28]

Participants

6

Reactant 5

HCID 1049PyridineHCID 3776IsopropanolHCID 15385Ethanesulfonylchloride, 2-chloro-HCID 81531DiisopropylethylamineHCID 82291Allylamine hydrochloride

Product 1

HCID 86705345N-allyltaurine isopropyl esterYield 20%

Procedure

2-Chloroethylsulfonyl chloride (2 g, 12.3 mmol) was is dissolved in 2-propanol (20 mL), pyridine (2.7 mL) was added, and the mixture was stirred at room temperature for 3 hours. Allylamine hydrochloride (1.15 g, 12.3 mmol) and diisopropylethylamine (6.4 mL) was added, and stirred at room temperature for 3 hours. The reaction mixture was evaporated under reduced pressure, 5% sodium bicarbonate solution was added to the residue, and the mixture was extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give the title compound (0.5 g, 2.4 mmol, 20%).

Workup

  1. stirringstirred at room temperature for 3 hours
  2. customThe reaction mixture was evaporated under reduced pressure, 5% sodium bicarbonate solution
  3. additionwas added to the residue
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe extract was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ed13c25d7b08414e8d7f473b0e7ec1a6
Source dataset
uspto-grants-2016_01
Patent number
US09227949B2

Reaction notes

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