Water → HCID 58009491, compound

HRID 1009491Notes

Reaction equation

HRID 1009491 reaction equation
[Cl:1][C:2]1[C:3]([CH3:31])=[C:4]([N:8]([S:21]([C:24]2[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=2)(=[O:23])=[O:22])[CH2:9][C:10]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=2)=[O:11])[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:39][C:40]([O:42][CH2:43][CH3:44])=[O:41].O>CN(C=O)C>[Cl:1][C:2]1[C:3]([CH3:31])=[C:4]([N:8]([S:21]([C:24]2[CH:25]=[CH:26][C:27]([CH3:30])=[CH:28][CH:29]=2)(=[O:22])=[O:23])[CH2:9][C:10]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:39][C:40]([O:42][CH2:43][CH3:44])=[O:41])=[CH:16][CH:15]=2)=[O:11])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 58009531HCID 58009531, compound

Product 1

HCID 58009491HCID 58009491, compoundYield 103.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

300 mg of N2-(3-chloro-2-methylphenyl)-N-(4-hydroxybenzyl)-N2-[(4-methylphenyl)sulfonyl]glycinamide was dissolved in 2.00 mL of DMF, and 110 mg of potassium carbonate and 133 mg of ethyl bromoacetate were added thereto, followed by stirring at room temperature overnight. To the reaction liquid was added water, followed by extraction with ethyl acetate, and the organic layer was washed with saturated brine, and then dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=60:40 to 30:70) to obtain 370 mg of ethyl 4-[({N-(3-chloro-2-methylphenyl)-N-[(4-methylphenyl)sulfonyl]glycyl}amino)methyl]phenoxyacetate.

Workup

  1. customTo the reaction liquid
  2. extractionfollowed by extraction with ethyl acetate
  3. washthe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=60:40 to 30:70)

Sources & evidence

ORD record
ord-851e942e659e4862aba4f0d578842532
Source dataset
uspto-grants-2011_07
Patent number
US07973078B2

Reaction notes

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