Water → HCID 11518518, compound

HRID 1713055Notes

Reaction equation

HRID 1713055 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[CH:5](CC)[CH2:6][CH2:7][N:8]1[C:12]2=[N:13][S:14][C:15](N)=[C:11]2[S:10][C:9]1=[S:17])[CH3:2].[N+:21]([C:24]1[CH:29]=[CH:28][C:27]([C:30]2[O:31][CH:32]=[CH:33][CH:34]=2)=[CH:26][CH:25]=1)([O-:23])=[O:22].O.CCCCCC>C(#N)C.C(OCC)(=O)C>[CH2:1]([O:3][C:4](=[O:20])[CH2:5][CH2:6][CH2:7][N:8]1[C:12]2=[N:13][S:14][C:15]([C:32]3[O:31][C:30]([C:27]4[CH:26]=[CH:25][C:24]([N+:21]([O-:23])=[O:22])=[CH:29][CH:28]=4)=[CH:34][CH:33]=3)=[C:11]2[S:10][C:9]1=[S:17])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 8058HexaneHCID 6049692-(4-Nitrophenyl)furanHCID 86618340HCID 86618340, compound

Product 1

HCID 11518518HCID 11518518, compoundYield 16.8%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent3×HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
-10 °C

Procedure

As depicted in Scheme 34 below, Compound 43 (30 mg, 0.2 mmol) was dissolved in dry acetonitrile (2 ml), under nitrogen atmosphere, and the solution was cooled to −10° C. Nitrosyltetrafluoroborate (NOBF4, 28 mg, 0.24 mmol) in dry acetonitrile (1 ml) was then added and the resulting mixture immediately turned red. The mixture was stirred for one hour at −10° C., and a mixture of 2-(4-nitrophenyl) furan (75 mg, 0.4 mmol) and CuCl2 dihydrate (5 mg) in acetonitrile (1 ml) was thereafter added dropwise. The resulting mixture was allowed to warm to 0° C., and stirring was continues while monitoring the reaction by TLC. Once the reaction was completed (after about one hour), a mixture of ethyl acetate and water was added, and after separation of the phases the organic phase was dried over Na2SO4, and the solvent was evaporated under reduced pressure to give 130 mg of the crude red product. Purification by column chromatography using fine silica and a 4:1 hexane:ethyl acetate mixture as eluent gave 16 mg of Compound 45 as a red oily solid (15-20% yield). The product was further purified by preparative HPLC using an acetonitrile:water gradient as a mobile phase.

Workup

  1. additionwas thereafter added dropwise
  2. temperatureto warm to 0° C.
  3. stirringstirring
  4. customthe reaction by TLC
  5. custom(after about one hour)
  6. additionwas added
  7. customafter separation of the phases the organic phase
  8. dry with materialwas dried over Na2SO4
  9. customthe solvent was evaporated under reduced pressure
  10. customto give 130 mg of the crude red product
  11. customPurification by column chromatography

Sources & evidence

ORD record
ord-8d71d4fd5242412e8cba53f2e3a4d3eb
Source dataset
uspto-grants-2010_09
Patent number
US07795255B2

Reaction notes

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