Ethanol → HCID 45084496, compound

HRID 1168199Notes

Reaction equation

HRID 1168199 reaction equation
[CH3:1][N:2]([CH:4]=[O:5])[CH3:3].[CH3:6][CH2:7][OH:8].[CH:9]1([N:15]=C=NC2CCCCC2)CCCC[CH2:10]1>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH3:1][N:2]([CH3:3])[C:4]([C@@H:9]1[CH2:10][O:8][CH2:7][CH2:6][NH:15]1)=[O:5]

Participants

6

Reactant 3

HCID 702EthanolHCID 6228DimethylformamideHCID 10868Dicyclohexylcarbodiimide

Product 1

HCID 45084496HCID 45084496, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 8 g of the compound obtained in the preceding stage in 40 ml of DCM and 2 ml of DMF is cooled to 4° C., 10 ml of EtOH, 1 g of 4-dimethylaminopyridine and 15 g of 1,3-dicyclohexylcarbodiimide are successively added, and then the reaction mixture is left stirring for 18 hours at AT. The insoluble material is filtered off and the filtrate is concentrated under vacuum. The residue is taken up in DCM and the insoluble material is again filtered off. The resulting organic phase is washed with an aqueous 5% KHSO4 solution, with an aqueous 5% NaHCO3 solution, dried over Na2SO4 and the solvent is evaporated under vacuum. The residue is chromatographed on silica gel, elution being carried out with a DCM/AcOEt (95/5; v/v) mixture. 8 g of the expected product are obtained.

Workup

  1. waitthe reaction mixture is left
  2. filtrationThe insoluble material is filtered off
  3. concentrationthe filtrate is concentrated under vacuum
  4. filtrationthe insoluble material is again filtered off
  5. washThe resulting organic phase is washed with an aqueous 5% KHSO4 solution, with an aqueous 5% NaHCO3 solution
  6. dry with materialdried over Na2SO4
  7. customthe solvent is evaporated under vacuum
  8. customThe residue is chromatographed on silica gel, elution

Sources & evidence

ORD record
ord-6fdeb07585a144f4999e8c0c483c5ab7
Source dataset
uspto-grants-2003_09
Patent number
US06624164B2

Reaction notes

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