Potassium Carbonate → HCID 67153467, compound

HRID 1914305Notes

Reaction equation

HRID 1914305 reaction equation
C[O:2][C:3](=[O:31])[CH2:4][CH2:5][NH:6][C:7](=[O:30])[C:8]1[CH:13]=[CH:12][C:11]([CH:14]([S:22][C:23]2[CH:28]=[CH:27][C:26](Br)=[CH:25][CH:24]=2)[CH2:15][CH:16]([CH3:21])[CH2:17][CH2:18][CH2:19][CH3:20])=[CH:10][CH:9]=1.C(=O)([O-])[O-].[K+].[K+].[F:38][C:39]([F:51])([F:50])[O:40][C:41]1[CH:42]=[C:43](B(O)O)[CH:44]=[CH:45][CH:46]=1>>[CH3:21][CH:16]([CH2:17][CH2:18][CH2:19][CH3:20])[CH2:15][CH:14]([C:11]1[CH:10]=[CH:9][C:8]([C:7]([NH:6][CH2:5][CH2:4][C:3]([OH:31])=[O:2])=[O:30])=[CH:13][CH:12]=1)[S:22][C:23]1[CH:24]=[CH:25][C:26]([C:44]2[CH:43]=[CH:42][C:41]([O:40][C:39]([F:51])([F:50])[F:38])=[CH:46][CH:45]=2)=[CH:27][CH:28]=1

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 27343853-(Trifluoromethoxy)phenylboronic Acid (contains varying amounts of Anhydride)HCID 67153566HCID 67153566, compound

Product 1

HCID 67153467HCID 67153467, compoundYield 50.6%

Procedure

3-{4-[1-(4-bromo-phenylsulfanyl)-3-methyl-heptyl]-benzoylamino}-propionic acid methyl ester (100 mg, 0.2 mmol), potassium carbonate (83 mg, 0.6 mmol), 3-trifluoromethoxyphenyl boronic acid (76 mg, 0.4 mmol) and tetrakis-(triphenylphosphine)palladium (23 mg, 0.02 mmol) are placed 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, diluted with ethyl acetate, acidified with 1 N HCl (0.6 mL), extracted with ethyl acetate. The organic layers are dried and purified with reverse phase HPLC to afford the title compound (58 mg). MS (ES): 544.1 [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. additiondiluted with ethyl acetate
  6. extractionextracted with ethyl acetate
  7. customThe organic layers are dried
  8. custompurified with reverse phase HPLC

Sources & evidence

ORD record
ord-01a9896f78f64c7abe7acaa9ebd7d496
Source dataset
uspto-grants-2013_12
Patent number
US08609892B2

Reaction notes

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