Triethylamine → HCID 56605928、化合物

HRID 974266ノート

反応式

HRID 974266 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.[C:29](Cl)(=[O:34])[CH2:30][CH2:31][CH2:32][CH3:33]>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:29](=[O:34])[CH2:30][CH2:31][CH2:32][CH3:33])[O:16]2)[CH2:2][CH2:3]1

参加物

6

反応物 3

HCID 8471TriethylamineHCID 61186Valeryl chlorideHCID 18649770HCID 18649770、化合物

生成物 1

HCID 56605928HCID 56605928、化合物収率 59%

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 (0.624 g, 2.1 mmoles), 4-dimethylaminopyridine (27 mg, 0.2 mmoles, Aldrich Chemical Co., Madison, Wis.), and triethylamine (2.0 mL, 14 mmoles, Aldrich Chemical Co., Madison, Wis.) were dissolved in 100 mL acetonitrile. Valeryl chloride (1.08 mL, 8.9 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). After evaporation of the solvent, the product was further purified on a Chromatotron (4 mm silica gel plate) with a mixture of hexane:acetone (85:15). The product containing fractions were combined, concentrated, and loaded onto preparative silica gel plates (20×20×0.2 cm). The plates were developed in a mixture of chloroform-acetone (80:20). The product was scraped from the preparative plate and eluted from the silica gel with ethanol. The product was then flash chromatographed on a silica gel column (2.5×40 cm) with a mixture of chloroform:acetone (95:5). Lyophilization afforded 0.463 g of 6-(cyclopropylmethylamino)-9-((2R,5S)-5-((pentanoyloxy)methyl)-tetrahydro-2-furyl)-9H-purine as an oil (58% 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. customAfter evaporation of the solvent
  5. customthe product was further purified on a Chromatotron (4 mm silica gel plate) with a mixture of hexane:acetone (85:15)
  6. additionThe product containing fractions
  7. concentrationconcentrated
  8. additionThe plates were developed in a mixture of chloroform-acetone (80:20)
  9. washeluted from the silica gel with ethanol
  10. customflash chromatographed on a silica gel column (2.5×40 cm) with a mixture of chloroform:acetone (95:5)

出典と根拠

ORDレコード
ord-3b5f6797578b45888b5f4ec4639b9a83
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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