Acetonitrile → HCID 86639018, compound

HRID 1662303Notes

Reaction equation

HRID 1662303 reaction equation
[C@@H:1]1([N:9]2[CH:13]=[C:12](I)[CH:11]=[C:10]2[N+:15]([O-:17])=[O:16])[O:6][C@H:5]([CH2:7][OH:8])[C@@H:3]([OH:4])[CH2:2]1.C(#N)C.C(N(CC)CC)C.[CH2:28]([NH:31][C:32](=[O:45])[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][NH:38][C:39](=[O:44])[C:40]([F:43])([F:42])[F:41])[C:29]#[CH:30]>CN(C=O)C.[Cu](I)I>[C@@H:1]1([N:9]2[CH:13]=[C:12]([C:30]#[C:29][CH2:28][NH:31][C:32](=[O:45])[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][NH:38][C:39](=[O:44])[C:40]([F:42])([F:43])[F:41])[CH:11]=[C:10]2[N+:15]([O-:17])=[O:16])[O:6][C@H:5]([CH2:7][OH:8])[C@@H:3]([OH:4])[CH2:2]1

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 11065305N-(2-propynyl)-6-trifluoroacetamidohexanamideHCID 67428497HCID 67428497, compound

Product 1

HCID 86639018HCID 86639018, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 6228DimethylformamideSolvent2×

Procedure

1-(2-Deoxy-β-D-ribofuranosyl)-4-iodo-2-nitropyrrole (354 mg, 1 mmol, containing α-anomer) was azeotroped twice with anhydrous acetonitrile in a 50 mL flask, followed by addition of copper iodide (31 mg, 160 μmol) and tetrakistriphenylphosphine palladium (0) (58 mg, 50 μmol). After these materials were dissolved in anhydrous DMF (5 mL), triethylamine (210 μL, 1.5 mmol) was added while stirring at room temperature and further stirred at room temperature under light-shielding conditions. To this mixture, a solution of N-(2-propynyl)-6-trifluoroacetamidohexanamide (396 mg, 1.5 mmol) in DMF (4 mL) was added dropwise and stirred overnight at room temperature. The reaction mixture was concentrated under reduced pressure, and the resulting crude product was purified by silica gel column chromatography (5-10% CH3OH in CH2Cl2) and C18-HPLC (39-41% CH3CN in H2O, 15 minutes) to give the desired product as an amorphous substance (408 mg, yield 83%).

Workup

  1. stirringfurther stirred at room temperature under light-shielding conditions
  2. stirringstirred overnight at room temperature
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customthe resulting crude product was purified by silica gel column chromatography (5-10% CH3OH in CH2Cl2) and C18-HPLC (39-41% CH3CN in H2O, 15 minutes)

Sources & evidence

ORD record
ord-476a878dea0244dc9f97f859607d49f4
Source dataset
uspto-grants-2011_10
Patent number
US08030478B2

Reaction notes

Loading…