Salicylamide → HCID 18760865, compound

HRID 432981Notes

Reaction equation

HRID 432981 reaction equation
[C:1]([NH2:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].[CH2:11]([O:13][CH:14]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH:28](OCC)OCC)=[CH:22][CH:21]=1)[C:15]([O:17][CH3:18])=[O:16])[CH3:12]>C(Cl)(Cl)Cl>[CH2:11]([O:13][CH:14]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH:28]2[NH:10][C:1](=[O:9])[C:2]3[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=3[O:4]2)=[CH:22][CH:21]=1)[C:15]([O:17][CH3:18])=[O:16])[CH3:12]

Participants

4

Reactant 2

HCID 5147SalicylamideHCID 18760863HCID 18760863, compound

Product 1

HCID 18760865HCID 18760865, compoundYield 74.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a stirred solution of polyphosphonate ethyl ester (PPE) (3.46 g, 8.0 mmol) in chloroform (10 mL) was added salicylamide (548 mg, 4.0 mmol) followed by addition of a solution of (±)-Methyl 2-ethoxy-3-[4-[(2,2-diethoxy)ethoxy]phenyl]propanoate (1.28 g, 4.4 mmol) obtained in preparation 2, in chloroform (10 mL) dropwise at 25-30° C. The reaction mixture was immersed in a preheated oil bath at 70° C. and refluxed 12 h. The reaction mixture was cooled to room temperature and CHCl3 was removed under reduced pressure. The resultant residue was neutralised (pH=7.0) with saturated aqueous NaHCO3 solution and extracted with ethyl acetate (3×20 mL). The combined organic extracts were washed with brine, dried over anhydrous Na2SO4 and concentrated. The crude compound was chromatographed on silica gel using a gradient of 5-25% of ethyl acetate in pet ether as eluent to afford the title compound (1.15 g, 72%) as a pale yellow liquid.

Workup

  1. customThe reaction mixture was immersed in a preheated oil bath at 70° C.
  2. temperaturerefluxed 12 h
  3. customCHCl3 was removed under reduced pressure
  4. extractionextracted with ethyl acetate (3×20 mL)
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated
  8. customThe crude compound was chromatographed on silica gel using a gradient of 5-25% of ethyl acetate in pet ether as eluent

Sources & evidence

ORD record
ord-0455489feac045e691ec88d70cca0d44
Source dataset
uspto-grants-2003_12
Patent number
US06664411B2

Reaction notes

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