Potassium Carbonate → HCID 57995523, compound

HRID 1512537Notes

Reaction equation

HRID 1512537 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:15]([CH2:21][CH:22]([CH3:24])[CH3:23])[C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:5]=[C:6]([S:9](=[O:14])(=[O:13])[N:10]([CH3:12])[CH3:11])[C:7]=1[OH:8].C([O-])([O-])=O.[K+].[K+].[CH:31]1([CH2:34]Br)[CH2:33][CH2:32]1>CS(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([CH:15]([CH2:21][CH:22]([CH3:23])[CH3:24])[C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:5]=[C:6]([S:9](=[O:13])(=[O:14])[N:10]([CH3:12])[CH3:11])[C:7]=1[O:8][CH2:34][CH:31]1[CH2:33][CH2:32]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 81503BromomethylcyclopropaneHCID 57995634HCID 57995634, compound

Product 1

HCID 57995523HCID 57995523, compoundYield 41.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of ethyl 2-(3-bromo-5-(N,N-dimethylsulfamoyl)-4-hydroxyphenyl)-4-methylpentanoate (0.75 g, 1.77 mmol) in DMSO (25 mL) were added K2CO3 (367 mg, 2.106 mmol) and cyclopropylmethylbromide (0.2 mL, 2.13 mmol) at RT under inert atmosphere. The reaction mixture was stirred at 80° C. temperature over a period of 14 h. After completion of starting material (by TLC), the reaction mixture was cooled to RT and quenched with water and extracted with EtOAc (3×100 mL). Combined organic layers were washed with water (3×75 mL), brine and dried over Na2SO4. After filtration and evaporation, the crude material was purified by column chromatography to afford ethyl 2-(3-bromo-4-(cyclopropylmethoxy)-5-(N,N-dimethylsulfamoyl)phenyl)-4-methylpentanoate (350 mg) as a liquid,

Workup

  1. temperatureAfter completion of starting material (by TLC), the reaction mixture was cooled to RT
  2. customquenched with water
  3. extractionextracted with EtOAc (3×100 mL)
  4. washCombined organic layers were washed with water (3×75 mL), brine
  5. dry with materialdried over Na2SO4
  6. filtrationAfter filtration and evaporation
  7. customthe crude material was purified by column chromatography

Sources & evidence

ORD record
ord-f96f199aa76a45458a79accc8c30dad7
Source dataset
uspto-grants-2012_07
Patent number
US08217064B2

Reaction notes

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