Potassium Carbonate → 3-{4-[1-(4'-Trifluoromethoxy-biphenyl-4-yloxy)-heptyl]-benzoylamino}-propionic acid methyl ester

HRID 1914310Notes

Reaction equation

HRID 1914310 reaction equation
[CH3:1][O:2][C:3](=[O:30])[CH2:4][CH2:5][NH:6][C:7](=[O:29])[C:8]1[CH:13]=[CH:12][C:11]([CH:14]([O:21][C:22]2[CH:27]=[CH:26][C:25](Br)=[CH:24][CH:23]=2)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:10][CH:9]=1.C(=O)([O-])[O-].[K+].[K+].[F:37][C:38]([F:50])([F:49])[O:39][C:40]1[CH:45]=[CH:44][C:43](B(O)O)=[CH:42][CH:41]=1>>[CH3:1][O:2][C:3](=[O:30])[CH2:4][CH2:5][NH:6][C:7](=[O:29])[C:8]1[CH:13]=[CH:12][C:11]([CH:14]([O:21][C:22]2[CH:27]=[CH:26][C:25]([C:43]3[CH:42]=[CH:41][C:40]([O:39][C:38]([F:37])([F:49])[F:50])=[CH:45][CH:44]=3)=[CH:24][CH:23]=2)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:10][CH:9]=1

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 27343864-(Trifluoromethoxy)phenylboronic acidHCID 671533873-{4-[1-(4-Bromo-phenoxy)-heptyl]-benzoylamino}-propionic acid methyl ester

Product 1

HCID 671534443-{4-[1-(4'-Trifluoromethoxy-biphenyl-4-yloxy)-heptyl]-benzoylamino}-propionic acid methyl esterYield 34.2%

Procedure

3-{4-[1-(4-Bromo-phenoxyl)-heptyl]-benzoylamino}-propionic acid methyl ester (isomer 1, 100 mg, 0.21 mmol), potassium carbonate (85 mg, 0.63 mmol), 4-triflouromethoxylphenyl boronic acid (86 mg, 0.42 mmol) and tetrakis-(triphenylphosphine)palladium (24 mg, 0.021 mmol) are place in a flask. After the reaction is purged with N2 for several times, THF/H2O (20 ml/5 ml) is added. The resulting solution is refluxed overnight, concentrated and acidified by 1 N HCl (0.6 mL), extracted with ethyl acetate. Combined organic layers are washed with water and brine, dried over sodium sulfate, purified by reverse phase HPLC to give the title compound (40 mg). MS (ES): 526.2 [M−H]−.

Workup

  1. customAfter the reaction is purged with N2 for several times, THF/H2O (20 ml/5 ml)
  2. additionis added
  3. temperatureThe resulting solution is refluxed overnight
  4. concentrationconcentrated
  5. extractionextracted with ethyl acetate
  6. washCombined organic layers are washed with water and brine
  7. dry with materialdried over sodium sulfate
  8. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-ef5796b6487b4234ac0f2f0b034db6d7
Source dataset
uspto-grants-2013_12
Patent number
US08609892B2

Reaction notes

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