Triethylamine → HCID 56612472、化合物

HRID 974263ノート

反応式

HRID 974263 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:38])[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]>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:38])[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[O:16]2)[CH2:2][CH2:3]1

参加物

6

反応物 3

HCID 8471TriethylamineHCID 69819Nonanoyl chlorideHCID 18649770HCID 18649770、化合物

生成物 1

HCID 56612472HCID 56612472、化合物収率 32.3%

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 (0.498 g, 1.7 mmoles), 4-dimethylaminopyridine (10 mg, 0.1 mmoles, Aldrich Chemical Co., Madison, Wis.), and triethylamine (2.0 mL, 14 mmoles, Aldrich Chemical Co., Madison, Wis.) were dissolved in 50 mL acetonitrile. Nonanoyl chloride (1.26 mL, 7.0 mmoles, Aldrich Chemical Co., Madison, Wis.) was added and the reaction was stirred at room temperature for 3 hours. The reaction was quenched with methanol and solvents were evaporated in vacuo. The residue was dissolved in 25 mL ethyl acetate and undissolved salts were removed by filtration. After evaporation of the ethyl acetate, the residue was dissolved in methanol and passed over a silica gel column (4.8×13 cm). The product containing fractions were combined, concentrated, and chromatographed on a Chromatotron (4 mm silica gel plate) in a mixture of hexane:acetone (80:20). Two separate subsequent runs on the Chromatotron (4 mm silica gel plate) with a mixture of chloroform:acetone (95:5) and a mixture of hexane:acetone (85:15) followed by lyophilization afforded 0.236 g of 6-(cyclopropylmethylamino)-9-((2R,5S)-5-[(nonanoyloxy)methyl]-tetrahydro-2-furyl)-9H-purine as an oil (32% yield).

後処理

  1. customThe reaction was quenched with methanol and solvents
  2. customwere evaporated in vacuo
  3. dissolutionThe residue was dissolved in 25 mL ethyl acetate
  4. customundissolved salts were removed by filtration
  5. customAfter evaporation of the ethyl acetate
  6. dissolutionthe residue was dissolved in methanol
  7. additionThe product containing fractions
  8. concentrationconcentrated
  9. customchromatographed on a Chromatotron (4 mm silica gel plate) in a mixture of hexane:acetone (80:20)
  10. customTwo separate subsequent runs on the Chromatotron (4 mm silica gel plate)
  11. additionwith a mixture of chloroform:acetone (95:5)
  12. additiona mixture of hexane:acetone (85:15)

出典と根拠

ORDレコード
ord-005c1b068c224ee1ba5e0bbc12fc6999
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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