Potassium Carbonate → HCID 57995523, compound

HRID 385480Notes

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

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

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

Sources & evidence

ORD record: ord-0962babd03c6401e86ba847961b243e6
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08367863B2

Reaction notes

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