Water → HCID 20773936, compound

HRID 1375957Notes

Reaction equation

HRID 1375957 reaction equation
I[C:2]1[CH:33]=[CH:32][CH:31]=[CH:30][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:18][CH2:17][N:16]([CH:19]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:20]([O:22][CH3:23])=[O:21])[CH2:15][CH2:14]2)=[CH:9][CH:8]=1)=[O:5].C([Sn](CCCC)(CCCC)[C:39]1[O:40][CH:41]=[CH:42][CH:43]=1)CCC.C([O-])([O-])=O.[Na+].[Na+].O>O1CCOCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[O:40]1[CH:41]=[CH:42][CH:43]=[C:39]1[C:2]1[CH:33]=[CH:32][CH:31]=[CH:30][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:18][CH2:17][N:16]([CH:19]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:20]([O:22][CH3:23])=[O:21])[CH2:15][CH2:14]2)=[CH:9][CH:8]=1)=[O:5]

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 43936882-(Tributylstannyl)furanHCID 16667332HCID 16667332, compound

Product 1

HCID 20773936HCID 20773936, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of intermediate (29) (0.0036 mol), tributyl-2-furanyl-stannane (0.029 mol), PdCl2(PPh3)2 (0.0007 mol) and Na2CO3 (0.0576 mol) in dioxane (30 ml) was stirred and refluxed for 1 hour. Water was addedd. The mixture was extracted with ethyl acetate. The organic layer was separated, dried, filtered, and the solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent:cyclohexane/ethyl acetate 80/20). The pure fractions were collected and the solvent was evaporated, yielding 4-[4-[[2-(2-furanyl)benzoyl]amino]phenyl]-α-phenyl-1-piperazineacetic acid, methyl ester (intermediate 30, mp. 90° C.).

Workup

  1. temperaturerefluxed for 1 hour
  2. extractionThe mixture was extracted with ethyl acetate
  3. customThe organic layer was separated
  4. customdried
  5. filtrationfiltered
  6. customthe solvent was evaporated
  7. customThe residue was purified by column chromatography over silica gel (eluent:cyclohexane/ethyl acetate 80/20)
  8. customThe pure fractions were collected
  9. customthe solvent was evaporated

Sources & evidence

ORD record
ord-0df83d4781244918a912bc032cc57911
Source dataset
uspto-grants-2007_01
Patent number
US07169796B2

Reaction notes

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