4-Toluenesulfonyl chloride → HCID 178427307, compound

HRID 1972232Notes

Reaction equation

HRID 1972232 reaction equation
[NH2:1][C@H:2]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([F:14])([F:13])[F:12])[CH:6]=1)[CH2:3]O.C([O-])([O-])=O.[K+].[K+].[S:21](Cl)([C:24]1[CH:30]=[CH:29][C:27]([CH3:28])=[CH:26][CH:25]=1)(=[O:23])=[O:22]>ClCCCl>[S:21]([N@@:1]1[CH2:3][CH:2]1[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([F:14])([F:13])[F:12])[CH:6]=1)([C:24]1[CH:30]=[CH:29][C:27]([CH3:28])=[CH:26][CH:25]=1)(=[O:23])=[O:22]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chloride2×HCID 11430Potassium Carbonate2×HCID 59486034HCID 59486034, compound

Product 1

HCID 178427307HCID 178427307, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of the crude product from Step B (1.11 g, 5.45 mmol) in 1,2-dichloroethane (25 mL) at 0° C. are added K2CO3 (2.26 g, 16.4 mmol) and TsCl (2.60 g, 13.6 mmol). The reaction mixture is stirred at room temperature overnight. If reaction is not done at this point, additional K2CO3 (0.75 g, 5.45 mmol) and TsCl (1.04 g, 5.45 mmol) are added and the reaction mixture is stirred for another 24 h. After removal of the solvent, the residue is taken in cold saturated NaHCO3 aqueous solution (100 mL) and extracted with EtOAc (3×50 mL). The combined organic layer is washed with brine, dried over MgSO4, concentrated, and purified by silica gel chromatography (0˜35% EtOAc/Hexanes) to provide (R)-1-tosyl-2-(3-(trifluoromethyl)phenyl)aziridine (1.74 g, 94% yield); 1H NMR (CDCl3, 400 MHz) δ 7.88 (d, 2H), 7.54 (m, 1H), 7.43 (m, 3H), 7.36 (d, 2H), 3.81 (dd, 1H), 3.01 (d, 1H), 2.45 (s, 3H), 2.39 (d, 1H); HPLC-MS calculated for C16H14F3NO2S (M+H+) 342.1, found 342.1.

Workup

  1. customIf reaction
  2. additionare added
  3. stirringthe reaction mixture is stirred for another 24 h
  4. customAfter removal of the solvent
  5. extractionextracted with EtOAc (3×50 mL)
  6. washThe combined organic layer is washed with brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated
  9. custompurified by silica gel chromatography (0˜35% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-dfc5b41a005d4b728b2ac10b0af2e476
Source dataset
uspto-grants-2013_04
Patent number
US08431607B2

Reaction notes

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