Ethyl [(phenoxycarbonyl)oxy]acetate → HCID 86610100, compound

HRID 1990697Notes

Reaction equation

HRID 1990697 reaction equation
[C:1]1([C:7]2[N:12]=[CH:11][C:10]([CH2:13][CH2:14][NH2:15])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1([O:22][C:23]([O:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])=O)C=CC=CC=1>C1(C)C=CC=CC=1>[C:1]1([C:7]2[N:12]=[CH:11][C:10]([CH2:13][CH2:14][NH:15][C:23]([O:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])=[O:22])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 12094709Ethyl [(phenoxycarbonyl)oxy]acetateHCID 67398847HCID 67398847, compound

Product 1

HCID 86610100HCID 86610100, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 0.85 g (4.29 mmol) of 2-(6-phenylpyrid-3-yl)ethanamine, prepared in stage 1.2., and of 1.25 g (5.58 mmol) of ethyl [(phenyloxycarbonyl)oxy]acetate (J. Med. Chem., 1999, 42, 277-290) in 40 ml of toluene is heated at 60° C. for 12 hours. The mixture is allowed to return to ambient temperature, the insoluble material is separated by filtration and the filtrate is concentrated under reduced pressure. The residue thus obtained is purifed by chromatography on silica gel, elution being carried out with a 30/70 mixture of ethyl acetate and of cyclohexane.

Workup

  1. customto return to ambient temperature
  2. customthe insoluble material is separated by filtration
  3. concentrationthe filtrate is concentrated under reduced pressure
  4. customThe residue thus obtained
  5. washis purifed by chromatography on silica gel, elution
  6. additionbeing carried out with a 30/70 mixture of ethyl acetate and of cyclohexane

Sources & evidence

ORD record
ord-a7d3fbe898d847c68fadbf3915e5b35a
Source dataset
uspto-grants-2010_01
Patent number
US07645757B2

Reaction notes

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