2-Mesitylenesulfonyl chloride → HCID 57474034, compound

HRID 1868417Notes

Reaction equation

HRID 1868417 reaction equation
[CH2:1]([O:3][C:4](=[O:11])[CH:5]([NH2:10])[C:6]([F:9])([F:8])[F:7])[CH3:2].[C:12]1([CH3:24])[CH:17]=[C:16]([CH3:18])[CH:15]=[C:14]([CH3:19])[C:13]=1[S:20](Cl)(=[O:22])=[O:21].S(Cl)(Cl)(=O)=O>N1C=CC=CC=1.Cl>[CH2:1]([O:3][C:4](=[O:11])[CH:5]([NH:10][S:20]([C:13]1[C:14]([CH3:19])=[CH:15][C:16]([CH3:18])=[CH:17][C:12]=1[CH3:24])(=[O:22])=[O:21])[C:6]([F:7])([F:8])[F:9])[CH3:2]

Participants

6

Reactant 3

HCID 130462-Mesitylenesulfonyl chlorideHCID 24648Sulfuryl chlorideHCID 10910004ethyl 2-amino-3,3,3-trifluoropropanoate

Product 1

HCID 57474034HCID 57474034, compoundYield 25.3%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 1049PyridineSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 2.10 g (12.3 mmol) of 2-amino-3,3,3-trifluoropropionic acid ethyl ester and 2.80 g (12.8 mmol) of 2-mesitylenesulfonyl chloride in 10 mL of pyridine was warmed at 70° C. After 3 hours, TLC (ethyl acetate-hexanes (2:8)) indicated a new product (PMA stain) that was more polar then sulfonyl chloride. The mixture was then diluted with 1 N aqueous HCl and extracted with three 30 mL portions of ethyl acetate. The combined organic layers were washed with three 30 mL portions of 1 N aqueous HCl, 20 mL of brine, and three 20 mL portions of saturated aqueous sodium bicarbonate solution, dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was chromatographed on silica gel eluting with ethyl acetate-hexanes (2-6% gradient) to afford 1.1 g (25%) of 3,3,3-trifluoro-2-(2,4,6-trimethylbenzenesulfonylamino)propionic acid ethyl ester.

Workup

  1. extractionextracted with three 30 mL portions of ethyl acetate
  2. washThe combined organic layers were washed with three 30 mL portions of 1 N aqueous HCl, 20 mL of brine, and three 20 mL portions of saturated aqueous sodium bicarbonate solution
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was chromatographed on silica gel eluting with ethyl acetate-hexanes (2-6% gradient)

Sources & evidence

ORD record
ord-b8e396dc88b6455c9c658d5ab2fe0716
Source dataset
uspto-grants-2009_12
Patent number
US07635711B2

Reaction notes

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