p-Toluenesulfonic acid → HCID 22316603, compound

HRID 396819Notes

Reaction equation

HRID 396819 reaction equation
O[C:2]1(C)[CH:7]=[C:6]([S:8]([CH3:11])(=[O:10])=[O:9])[CH:5]=[CH:4][CH:3]1[CH2:12][C:13](=[O:15])[CH3:14].[Br:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][C:25]([OH:27])=O)=[CH:20][CH:19]=1.[CH3:28]C1C=CC(S(O)(=O)=O)=CC=1.N12CCCN=C1CCCCC2>CN(C)C1C=CN=CC=1.O>[Br:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[C:25](=[O:27])[O:15][C:13]([CH3:14])([CH3:28])[C:12]=2[C:3]2[CH:2]=[CH:7][C:6]([S:8]([CH3:11])(=[O:9])=[O:10])=[CH:5][CH:4]=2)=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 74654Benzeneacetic acid, 4-bromo-HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 22316970HCID 22316970, compound

Product 1

HCID 22316603HCID 22316603, compoundYield 65.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolvent

Procedure

A mixture of [2-hydroxy-2-methyl-4-(methylsulfonyl)phenyl]propanone (1.5 g, 6.2 mmol, B. Cameron et al., WO 9619469), 4-bromophenylacetic acid (1.8 g, 8.1 mmol), 1-cyclohexyl-3-(2-morphorynoethyl)carbodiimide metho-p-toluenesulfonate (3.4 g, 8.1 mmol) and 4-(dimethylamino)pyridine (30 mg, 0.25 mmol) was stirred for 18 h at room temperature. 1,8-Diazabicyclo[5.4.0]undec-7-ene (1.9 mL, 12.7 mmol) was added and the mixture was refluxed for 3 h. After cooled to room temperature, H2O (50 mL) was added and extracted with CH2Cl2 (50 mL×2), washed with 2N aqueous HCl (50 mL), dried over MgSO4, and concentarted in vacuo. The reaction mixture was purified by flash chromatography eluting with ethyl acetate/hexane (1/1) to give title compound (1.7 g, 65%).

Workup

  1. temperaturethe mixture was refluxed for 3 h
  2. temperatureAfter cooled to room temperature
  3. extractionextracted with CH2Cl2 (50 mL×2)
  4. washwashed with 2N aqueous HCl (50 mL)
  5. dry with materialdried over MgSO4
  6. customThe reaction mixture was purified by flash chromatography
  7. washeluting with ethyl acetate/hexane (1/1)

Sources & evidence

ORD record
ord-e709eb78c08743cab9cd94cb12f2e089
Source dataset
uspto-grants-2003_08
Patent number
US06608095B2

Reaction notes

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