Methanol → Methyl 4-({(5-methoxy-5-oxopentyl)[2-(5-fluoro-2-hydroxyphenyl)ethyl]amino}methyl)benzoate

HRID 505609Notes

Reaction equation

HRID 505609 reaction equation
[CH2:1]([O:3][C:4](=[O:32])[CH2:5][CH2:6][CH2:7][CH2:8][N:9]([CH2:21][C:22]1[CH:31]=[CH:30][C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:24][CH:23]=1)[CH2:10][CH2:11][C:12]1[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=1[O:19]C)C.B(Br)(Br)Br.CO>ClCCl>[CH3:1][O:3][C:4](=[O:32])[CH2:5][CH2:6][CH2:7][CH2:8][N:9]([CH2:21][C:22]1[CH:31]=[CH:30][C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:24][CH:23]=1)[CH2:10][CH2:11][C:12]1[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=1[OH:19]

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 22015037Methyl 4-({(5-ethoxy-5-oxopentyl)[2-(5-fluoro-2-methoxy-phenyl)ethyl]amino}methyl)benzoate

Product 1

HCID 22015002Methyl 4-({(5-methoxy-5-oxopentyl)[2-(5-fluoro-2-hydroxyphenyl)ethyl]amino}methyl)benzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

2.6 g (5.84 μmmol) of methyl 4-({(5-ethoxy-5-oxopentyl)[2-(5-fluoro-2-methoxy-phenyl)ethyl]amino}methyl)benzoate are dissolved in 50 ml of dichloromethane, the mixture is cooled to 0° C., and 19.3 ml (19.3 mmol) of a 1N solution of boron tribromide in dichloromethane are added dropwise. The solution is stirred at 0° C. for one hour. 50 ml of methanol are slowly added dropwise at 0° C., and the reaction mixture is heated at reflux overnight. The mixture is cooled and the solvents are evaporated under reduced pressure. The residue is taken up in ethyl acetate and washed with sodium carbonate, the aqueous phase is extracted three times with ethyl acetate and the combined organic phases are washed with saturated sodium chloride solution, dried over magnesium sulphate, filtered and concentrated. The residue is chromatographed over silica gel (cyclohexane:ethyl acetate (5:1) to ethyl acetate:methanol (9:1)).

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureat reflux overnight
  3. temperatureThe mixture is cooled
  4. customthe solvents are evaporated under reduced pressure
  5. washwashed with sodium carbonate
  6. extractionthe aqueous phase is extracted three times with ethyl acetate
  7. washthe combined organic phases are washed with saturated sodium chloride solution
  8. dry with materialdried over magnesium sulphate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe residue is chromatographed over silica gel (cyclohexane:ethyl acetate (5:1) to ethyl acetate:methanol (9:1))

Sources & evidence

ORD record
ord-c298ed4edf6f4931a1e610dd1c3c7897
Source dataset
uspto-grants-2010_08
Patent number
US07781470B2

Reaction notes

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