Triethylamine → HCID 67429382、化合物

HRID 1662302ノート

反応式

HRID 1662302 の反応式
[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(CC)CC)C.[CH2:25]([NH:28][C:29](=[O:33])[CH:30]([Cl:32])[Cl:31])[C:26]#[CH:27]>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I>[C@@H:1]1([N:9]2[CH:13]=[C:12]([C:27]#[C:26][CH2:25][NH:28][C:29](=[O:33])[CH:30]([Cl:32])[Cl:31])[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

参加物

7

反応物 3

HCID 8471TriethylamineHCID 132331222,2-Dichloro-N-(prop-2-yn-1-yl)acetamideHCID 67428497HCID 67428497、化合物2 回

生成物 1

HCID 67429382HCID 67429382、化合物収率 81%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418397HCID 178418397、化合物触媒HCID 6228Dimethylformamide溶媒2 回

実験手順

1-(2-Deoxy-β-D-ribofuranosyl)-4-iodo-2-nitropyrrole (Compound 1) (354 mg, 1.0 mmol), Pd(PPh3)4 (58 mg, 0.05 mmol), CuI (30 mg, 0.16 mmol) and triethylamine (209 μl, 1.5 mmol) were dissolved in DMF (3.5 ml), followed by addition of a 1 M DMF solution of N-(2-propynyl)-dichloroacetamide (1.5 ml, 1.5 mmol). After stirring at room temperature for 12 hours, the reaction mixture was partitioned between ethyl acetate and water, and the organic layer was washed three times with water. After drying over anhydrous sodium sulfate, the organic layer was concentrated and purified on a silica gel column (CH2Cl2:MeOH, 20:1, v/v) and by HPLC (34%-35% CH3CN, 12 minutes) to give Compound 3 (317 mg, 81%).

後処理

  1. customthe reaction mixture was partitioned between ethyl acetate and water
  2. washthe organic layer was washed three times with water
  3. dry with materialAfter drying over anhydrous sodium sulfate
  4. concentrationthe organic layer was concentrated
  5. custompurified on a silica gel column (CH2Cl2

出典と根拠

ORDレコード
ord-a544384df7cd4a3d95c7624335447614
出典データセット
uspto-grants-2011_10
特許番号
US08030478B2

反応ノート

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