Acetonitrile → HCID 86639018, 화합물

HRID 1662303노트

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HRID 1662303 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

HCID 86639018HCID 86639018, 화합물수율 83%

시약·촉매·용매 2

HCID 83717Copper iodide촉매HCID 6228Dimethylformamide용매2회

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-476a878dea0244dc9f97f859607d49f4
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08030478B2

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