Hydrochloric Acid → HCID 22054068, compound

HRID 1830130Notes

Reaction equation

HRID 1830130 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH2:8][CH:9]([CH2:13][S:14]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)(=[O:16])=[O:15])[C:10]([OH:12])=[O:11])[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[C:30]1(B(O)O)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.Cl>C1(C)C=CC=CC=1.C(O)C>[C:2]1([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][CH:9]([CH2:13][S:14]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)(=[O:16])=[O:15])[C:10]([OH:12])=[O:11])[CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 22053949HCID 22053949, compound

Product 1

HCID 22054068HCID 22054068, compoundYield 80.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

3-(3-Bromo-phenyl)-2-benzylsulfonylmethyl-propionic acid (0.5 g, 1.26 mmol) was dissolved in toluene (20 mL) and ethanol (5 mL). Tetrakistriphenylphosphine palladium (146 mg, 0.126 mmol) was added and the mixture was stirred at ambient temperature under nitrogen for 30 minutes. Powdered potassium carbonate (870 mg, 6.3 mmol) and phenylboronic acid (200 mg, 1.64 mmol) were added, and the reaction mixture was heated at 75° C. for 2 hours. After cooling, the mixture was acidified with 1N aqueous HCl and extracted with ethyl acetate (3×50 mL). The combined organic layers were washed with brine, dried with magnesium sulfate and evaporated. The acid was purified by flash chromatography on silica gel (ethyl acetate/hexane; 1:1) to yield 3-biphenyl-3-yl-2-benzylsulfonylmethyl-propionic acid (0.40 g).

Workup

  1. temperaturethe reaction mixture was heated at 75° C. for 2 hours
  2. temperatureAfter cooling
  3. extractionextracted with ethyl acetate (3×50 mL)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried with magnesium sulfate
  6. customevaporated
  7. customThe acid was purified by flash chromatography on silica gel (ethyl acetate/hexane; 1:1)

Sources & evidence

ORD record
ord-d97f008c4688469185852c8405d5463e
Source dataset
uspto-grants-2006_06
Patent number
US07064123B1

Reaction notes

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