Stannanecarbonitrile, tributyl- → (2R,3R,4R,5R)-4-acetyloxy-2-(acetyloxy-methyl)-5-[2-cyano-6-(cyclopentylamino)purin-9-yl]oxolan-3-yl acetate

HRID 1724638ノート

反応式

HRID 1724638 の反応式
[C:1]([O:4][C@H:5]1[C@@H:9]([O:10][C:11](=[O:13])[CH3:12])[C@H:8]([N:14]2[CH:22]=[N:21][C:20]3[C:15]2=[N:16][C:17](I)=[N:18][C:19]=3[NH:23][CH:24]2[CH2:28][CH2:27][CH2:26][CH2:25]2)[O:7][C@@H:6]1[CH2:30][O:31][C:32](=[O:34])[CH3:33])(=[O:3])[CH3:2].C([Sn]([C:48]#[N:49])(CCCC)CCCC)CCC>CN(C)C=O.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>[C:1]([O:4][C@H:5]1[C@@H:9]([O:10][C:11](=[O:13])[CH3:12])[C@H:8]([N:14]2[CH:22]=[N:21][C:20]3[C:15]2=[N:16][C:17]([C:48]#[N:49])=[N:18][C:19]=3[NH:23][CH:24]2[CH2:28][CH2:27][CH2:26][CH2:25]2)[O:7][C@@H:6]1[CH2:30][O:31][C:32](=[O:34])[CH3:33])(=[O:3])[CH3:2]

参加物

5

反応物 2

HCID 200512Stannanecarbonitrile, tributyl-HCID 14886862(2R,3R,4R,5R)-4-acetyloxy-2-(acetyloxymethyl)-5-[6-(cyclopentylamino)-2-iodopurin-9-yl]oxolan-3-yl acetate

生成物 1

HCID 58767046(2R,3R,4R,5R)-4-acetyloxy-2-(acetyloxy-methyl)-5-[2-cyano-6-(cyclopentylamino)purin-9-yl]oxolan-3-yl acetate収率 87.3%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
120 °C

実験手順

To a solution of (2R,3R,4R,5R)-4-acetyloxy-2-(acetyloxymethyl)-5-[6-(cyclopentylamino)-2-iodopurin-9-yl]oxolan-3-yl acetate (0.9 g, 1.53 mmol) in N,N-dimethylformamide (40 ml) was added tributyltin cyanide (0.58 g, 1.84 mmol) and tetrakis(triphenylphosphine)palladium (0.27 g, 0.23 mmol), and the mixture was stirred at 120° C. f overnight. Solvent was removed under reduced pressure, and the residue was dissolved in ethyl acetate and filtered through celite. The solvent was removed under reduced pressure, and the residue was chromatographed on silica gel, eluting with a mixture of ethanol/hexane 1:1, to provide (2R,3R,4R,5R)-4-acetyloxy-2-(acetyloxy-methyl)-5-[2-cyano-6-(cyclopentylamino)purin-9-yl]oxolan-3-yl acetate (0.65 g).

後処理

  1. customSolvent was removed under reduced pressure
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. filtrationfiltered through celite
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was chromatographed on silica gel
  6. washeluting with a mixture of ethanol/hexane 1:1

出典と根拠

ORDレコード
ord-0c5a7ae89be54a569321ec85d3be16e4
出典データセット
uspto-grants-2009_02
特許番号
US07488720B2

反応ノート

読み込み中…