HCID 54514243, compound → HCID 54506147, compound

HRID 2268618Notes

Reaction equation

HRID 2268618 reaction equation
[CH3:1][O:2][C:3](=[O:28])[C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[C:6]([O:11][CH2:12][CH2:13][N:14]([C:21]([O:23]C(C)(C)C)=[O:22])[C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)[CH:5]=1>ClCCl.FC(F)(F)C(O)=O>[CH3:1][O:2][C:3](=[O:28])[C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[C:6]([O:11][CH2:12][CH2:13][N:14]([C:21]([O:23][CH2:3][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)=[O:22])[C:15]2[CH:16]=[CH:17][N:18]=[CH:19][CH:20]=2)[CH:5]=1

Participants

4

Reactant 1

HCID 54514243HCID 54514243, compound

Product 1

HCID 54506147HCID 54506147, compoundYield 62.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 3-[2-(tert-butoxycarbonyl-pyridin-4-yl-amino)-ethoxy]-5-chloro-benzoic acid methyl ester (0.950 g) in dichloromethane (16 ml) and trifluoroacetic acid (4 ml) was stored at room temperature for 1 h. The solution was concentrated in vacuo and residual trifluoroacetic acid removed by co-evaporation with further dichloromethane. The residue was dissolved in dichloromethane (20 ml) and the solution stirred with saturated aqueous sodium bicarbonate (25 ml). Benzyl chloroformate (0.394 ml) was added to the bi-phasic mixture and stirring continued for 20 h. The aqueous layer was removed and the organic layer washed with 1M aqueous hydrochloric acid, saturated aqueous sodium bicarbonate, water and dried with brine and over sodium sulphate and concentrated under reduced pressure. The residue was purified by flash column chromatography, eluting with ethyl acetate:petroleum ether (3:1 v/v), to give the title compound as a colourless gum (0.32 g).

Workup

  1. concentrationThe solution was concentrated in vacuo and residual trifluoroacetic acid
  2. customremoved by co-evaporation with further dichloromethane
  3. dissolutionThe residue was dissolved in dichloromethane (20 ml)
  4. additionBenzyl chloroformate (0.394 ml) was added to the bi-phasic mixture
  5. stirringstirring
  6. customThe aqueous layer was removed
  7. washthe organic layer washed with 1M aqueous hydrochloric acid, saturated aqueous sodium bicarbonate, water
  8. dry with materialdried with brine and over sodium sulphate
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by flash column chromatography
  11. washeluting with ethyl acetate:petroleum ether (3:1 v/v)

Sources & evidence

ORD record
ord-2a4dc327c8a44b8388599fd5beeb3938
Source dataset
uspto-grants-2001_12
Patent number
US06326386B1

Reaction notes

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