Citric Acid → HCID 59659317, compound

HRID 2056644Notes

Reaction equation

HRID 2056644 reaction equation
C([O:3][C:4](=[O:33])[CH:5]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([N:22]([C:27](=[O:32])[C:28]([CH3:31])([CH3:30])[CH3:29])[CH2:23][CH:24]([CH3:26])[CH3:25])[CH:15]=1)[CH2:6][C:7]1[CH:12]=[CH:11][C:10](I)=[CH:9][CH:8]=1)C.[Cl:34][C:35]1[CH:40]=[CH:39][CH:38]=[C:37]([Cl:41])[C:36]=1[C:42]#[CH:43].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(N(CC)CC)C.[Cu](I)I.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Cl:34][C:35]1[CH:40]=[CH:39][CH:38]=[C:37]([Cl:41])[C:36]=1[C:42]#[C:43][C:10]1[CH:9]=[CH:8][C:7]([CH2:6][CH:5]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([N:22]([C:27](=[O:32])[C:28]([CH3:31])([CH3:30])[CH3:29])[CH2:23][CH:24]([CH3:25])[CH3:26])[CH:15]=2)[C:4]([OH:3])=[O:33])=[CH:12][CH:11]=1

Participants

7

Reactant 3

HCID 311Citric AcidHCID 22271730Benzene, 1,3-dichloro-2-ethynyl-HCID 69307704HCID 69307704, compound

Product 1

HCID 59659317HCID 59659317, compound

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 8471TriethylamineSolvent

Procedure

3-(4-iodophenyl)-2-{3-[(2,2-dimethylpropionyl) isobutylamino]-4-methoxyphenyl}propionic acid ethyl ester (0.15 g, 0.27 mmol) was dissolved in triethylamine (2 mL), the solution was further added with 1,3-dichloro-2-ethynylbenzene (0.15 g, 0.53 mmol), copper iodide (I) (5 mg, 0.026 mmol) and tetrakis(triphenylphosphine) palladium (15 mg, 0.013 mmol), and the mixture was stirred at room temperature for 15 hours. The solution was treated with a citric acid solution. The solution was then extracted with ethyl acetate, washed with a saturated brine, the extract was dried over anhydrous magnesium sulfate, evaporated under reduced pressure so as to remove the solvent, and the resultant residue was purified through silica gel column chromatography (hexane:ethyl acetate (v/v)=3:1) to thereby obtain 3-[4-(2,6-dichlorophenylethynyl)phenyl]-2-{3-[(2,2-dimethylpropionyl)isobutylamino]-4-methoxyphenyl} propionic acid ethyl ester (yield: 0.11 g, yield ratio: 68%).

Workup

  1. extractionThe solution was then extracted with ethyl acetate
  2. washwashed with a saturated brine
  3. dry with materialthe extract was dried over anhydrous magnesium sulfate
  4. customevaporated under reduced pressure so as
  5. customto remove the solvent
  6. customthe resultant residue was purified through silica gel column chromatography (hexane:ethyl acetate (v/v)=3:1) to thereby obtain 3-[4-(2,6-dichlorophenylethynyl)phenyl]-2-{3-[(2,2-dimethylpropionyl)isobutylamino]-4-methoxyphenyl} propionic acid ethyl ester (yield: 0.11 g, yield ratio: 68%)

Sources & evidence

ORD record
ord-e2c9cab251674734a3dca314c03bb943
Source dataset
uspto-grants-2008_02
Patent number
US07335673B2

Reaction notes

Loading…