Cesium carbonate → HCID 67703759, compound

HRID 55260Notes

Reaction equation

HRID 55260 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:7][O:8][C:9](=[O:19])[CH2:10][CH2:11][C:12]1[C:17]([OH:18])=[CH:16][CH:15]=[CH:14][N:13]=1.Br[CH2:21][CH2:22][CH2:23][CH2:24]/[CH:25]=[CH:26]/[C:27]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=1>CN(C)C=O>[CH3:7][O:8][C:9](=[O:19])[CH2:10][CH2:11][C:12]1[C:17]([O:18][CH2:21][CH2:22][CH2:23][CH2:24]/[CH:25]=[CH:26]/[C:27]2[CH:28]=[CH:29][C:30]([O:33][CH3:34])=[CH:31][CH:32]=2)=[CH:16][CH:15]=[CH:14][N:13]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 15472944HCID 15472944, compoundHCID 545149013-(3-Hydroxy-2-pyridyl)-propionic acid methyl ester

Product 1

HCID 67703759HCID 67703759, compoundYield 45.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.02 g of cesium carbonate is added to a solution of 300 mg of 3-(3-hydroxy-2-pyridyl)-propionic acid methyl ester and 450 mg of (1E)-6-bromo-1-(4-methoxyphenyl)-1-hexene in 6 ml of dimethylformamide, and the suspension is stirred under argon atmosphere for 20 hours at room temperature. The reaction mixture is filtered, the filter residue is washed with dichloromethane and the filtrate is concentrated by evaporation. The residue is added to water, shaken out with ethyl acetate, the organic phase is washed with saturated common salt solution, dried with sodium sulfate and concentrated by evaporation. The crude product is purified by high-pressure liquid chromatography on reversed-phase silica gel (Nova-Pak HR C18) with methanol/water=8/2. 280 mg of 3-{3-[6-(4-methoxyphenyl)-(5E)-5-hexenyloxy]-2-pyridyl}-propionic acid methyl ester is obtained as colorless oil.

Workup

  1. filtrationThe reaction mixture is filtered
  2. washthe filter residue is washed with dichloromethane
  3. concentrationthe filtrate is concentrated by evaporation
  4. additionThe residue is added to water
  5. stirringshaken out with ethyl acetate
  6. washthe organic phase is washed with saturated common salt solution
  7. dry with materialdried with sodium sulfate
  8. concentrationconcentrated by evaporation
  9. customThe crude product is purified by high-pressure liquid chromatography on reversed-phase silica gel (Nova-Pak HR C18) with methanol/water=8/2

Sources & evidence

ORD record
ord-8613d98c66dd43bbb648dc5f31779e88
Source dataset
uspto-grants-1997_04
Patent number
US05624943

Reaction notes

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