HCID 12074070, compound → HCID 12074071, compound

HRID 413924Notes

Reaction equation

HRID 413924 reaction equation
[CH2:1]([O:4][C:5](=[O:25])[CH2:6][CH2:7][C@H:8]([NH:15][C:16]([C:18]1[CH:23]=[CH:22][C:21](I)=[CH:20][CH:19]=1)=[O:17])[CH2:9][O:10][CH2:11][O:12][CH2:13][CH3:14])[CH:2]=[CH2:3].[Cu](C#N)[C:27]#[N:28]>CN(C=O)C.C(OCC)(=O)C.O>[CH2:1]([O:4][C:5](=[O:25])[CH2:6][CH2:7][C@H:8]([NH:15][C:16]([C:18]1[CH:23]=[CH:22][C:21]([C:27]#[N:28])=[CH:20][CH:19]=1)=[O:17])[CH2:9][O:10][CH2:11][O:12][CH2:13][CH3:14])[CH:2]=[CH2:3]

Participants

6

Reactant 2

HCID 12074070HCID 12074070, compoundHCID 178418260HCID 178418260, compound

Product 1

HCID 12074071HCID 12074071, compoundYield 71.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of the compound prepared in Example 3 (2.00 g) in DMF (40 ml), copper cyanide (520 mg) was added. The mixture was vigorously stirred for 3 hours at 50° C. The reaction mixture was cooled, and diluted with ethyl acetate and water. The solution was filtered, the filtrate was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated to give the title compound (1.12 g) having the following physical data.

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationThe solution was filtered
  3. extractionthe filtrate was extracted with ethyl acetate
  4. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-96668dee295f4217b60b69b830789dd3
Source dataset
uspto-grants-2003_05
Patent number
US06569899B1

Reaction notes

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