Methyl Salicylate → Methyl 2-[2-(4-{2-[(2,4-difluorobenzyl)(heptyl)amino]-2-oxoethoxy}-3-methoxyphenyl)ethoxy]benzoate

HRID 898897Notes

Reaction equation

HRID 898897 reaction equation
CS([O:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]([N:18]([CH2:26][C:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][C:28]=2[F:34])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[O:17])=[C:10]([O:35][CH3:36])[CH:9]=1)(=O)=O.[CH3:37][O:38][C:39](=[O:47])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=1O.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[F:34][C:28]1[CH:29]=[C:30]([F:33])[CH:31]=[CH:32][C:27]=1[CH2:26][N:18]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[C:16](=[O:17])[CH2:15][O:14][C:11]1[CH:12]=[CH:13][C:8]([CH2:7][CH2:6][O:5][C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][C:40]=2[C:39]([O:38][CH3:37])=[O:47])=[CH:9][C:10]=1[O:35][CH3:36]

Participants

5

Reactant 3

HCID 4133Methyl SalicylateHCID 11430Potassium CarbonateHCID 866009662-(4-{2-[(2,4-Difluorobenzyl)(heptyl)amino]-2-oxoethoxy}-3-methoxyphenyl)ethyl methanesulfonate

Product 1

HCID 69259490Methyl 2-[2-(4-{2-[(2,4-difluorobenzyl)(heptyl)amino]-2-oxoethoxy}-3-methoxyphenyl)ethoxy]benzoateYield 51%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-(4-{2-[(2,4-Difluorobenzyl)(heptyl)amino]-2-oxoethoxy}-3-methoxyphenyl)ethyl methanesulfonate (138 mg, 0.262 mmol) was dissolved in acetonitrile (10 ml). 2-Hydroxybenzoic acid methyl ester (40 mg, 0.262 mmol) was added and then potassium carbonate anhydrous (54 mg, 0.392 mmol) was added. The mixture was heated to reflux overnight and then evaporated to dryness. Water (10 ml) and ethyl acetate (10 ml) were added and the two phases were separated. The organic phase was washed with water and brine, dried (magnesium sulphate) and evaporated. Chromatography of the residue on a column (ISOLUTE® SI, 2 g/6 ml) using DCM, MeOH/DCM (1:99) as eluant gave 78 mg the desired product, yield 45% (two steps).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux overnight
  3. customevaporated to dryness
  4. additionWater (10 ml) and ethyl acetate (10 ml) were added
  5. customthe two phases were separated
  6. washThe organic phase was washed with water and brine
  7. dry with materialdried (magnesium sulphate)
  8. customevaporated

Sources & evidence

ORD record
ord-b8e07327be2948228bbf0ffa856dddee
Source dataset
uspto-grants-2008_04
Patent number
US07351858B2

Reaction notes

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