Triethylamine → HCID 56606033、化合物

HRID 974265ノート

反応式

HRID 974265 の反応式
[CH:1]1([CH2:4][NH:5][C:6]2[N:14]=[CH:13][N:12]=[C:11]3[C:7]=2[N:8]=[CH:9][N:10]3[C@H:15]2[CH2:19][CH2:18][C@@H:17]([CH2:20][OH:21])[O:16]2)[CH2:3][CH2:2]1.C(N(CC)CC)C.[CH3:29][O:30][CH2:31][C:32](Cl)=[O:33]>CN(C)C1C=CN=CC=1.C(#N)C>[CH:1]1([CH2:4][NH:5][C:6]2[N:14]=[CH:13][N:12]=[C:11]3[C:7]=2[N:8]=[CH:9][N:10]3[C@H:15]2[CH2:19][CH2:18][C@@H:17]([CH2:20][O:21][C:32](=[O:33])[CH2:31][O:30][CH3:29])[O:16]2)[CH2:2][CH2:3]1

参加物

6

反応物 3

HCID 8471TriethylamineHCID 96623Methoxyacetyl chlorideHCID 18649770HCID 18649770、化合物

生成物 1

HCID 56606033HCID 56606033、化合物収率 54.6%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6342Acetonitrile溶媒

実験手順

6-(Cyclopropylmethylamino)-9-[(2R,5S)-tetrahydro-5-(hydroxymethyl)-2-furyl]-9H-purine (0.319 g, 1.1 mmoles), 4-dimethylaminopyridine (10 mg, 0.1 mmoles, Aldrich Chemical Co., Madison, Wis.), and triethylamine (1.0 mL, 7 mmoles, Aldrich Chemical Co., Madison, Wis.) were dissolved in 50 mL acetonitrile. Methoxyacetyl chloride (460 μm, 5.0 mmoles, Aldrich Chemical Co., Madison, Wis.) was added and the reaction was stirred at room temperature for 6 hours. The reaction was quenched with methanol and solvents were evaporated in vacuo. The residue was dissolved in acetone and passed over a silica gel column (4.8×13 cm). The UV absorbing eluent was concentrated and separated on a Chromatotron (4 mm silica gel plate) with a mixture of chloroform:acetone (95:5). Solvents were removed in vacuo and the residue was further purified on a preparative silica gel plate (20×20×0.2 cm) developed in a mixture of chloroform:acetone (70:30). The product was scraped from the preparative plate and eluted from the silica gel with ethanol. Lyophilization afforded 0.217 g of 6-(cyclopropylmethylamino)-9-[(2R,5S)-5-[(methoxyacetoxy)methyl]-tetrahydro-2-furyl]-9H-purine as an oil (53% yield).

後処理

  1. customThe reaction was quenched with methanol and solvents
  2. customwere evaporated in vacuo
  3. dissolutionThe residue was dissolved in acetone
  4. customThe UV absorbing eluent
  5. concentrationwas concentrated
  6. customseparated on a Chromatotron (4 mm silica gel plate) with a mixture of chloroform:acetone (95:5)
  7. customSolvents were removed in vacuo
  8. customthe residue was further purified on a preparative silica gel plate (20×20×0.2 cm)
  9. additiondeveloped in a mixture of chloroform:acetone (70:30)
  10. washeluted from the silica gel with ethanol

出典と根拠

ORDレコード
ord-3e43f10d017d4e479416c39a957baf3a
出典データセット
uspto-grants-1991_11
特許番号
US05068320

反応ノート

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