5-Fluorouracil → 1-(1-Hydroxymethylpropyloxy)-methyl-5-fluorouracil

HRID 1649106ノート

反応式

HRID 1649106 の反応式
[CH2:1]([CH:3]1[CH2:7][O:6]C[O:4]1)[CH3:2].[CH2:8](O)C(O)CC.C[Si]([C:18]1[NH:23][C:22](=[O:24])[N:21]([Si](C)(C)C)[C:20](=[O:29])[C:19]=1[F:30])(C)C.FC1C(=O)NC(=O)NC=1.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl.CO>[OH:6][CH2:7][CH:3]([O:4][N:23]1[CH:18]=[C:19]([F:30])[C:20](=[O:29])[N:21]([CH3:8])[C:22]1=[O:24])[CH2:1][CH3:2]

参加物

8

反応物 5

HCID 33855-FluorouracilHCID 114291,2-ButanediolHCID 1217554-Ethyl-1,3-dioxolaneHCID 516892Sodium BicarbonateHCID 68585259HCID 68585259、化合物

生成物 1

HCID 204806031-(1-Hydroxymethylpropyloxy)-methyl-5-fluorouracil

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6212Chloroform溶媒

実験手順

4-Ethyl-1,3-dioxolane (10 ml) prepared from butane-1,2-diol was added to bis(trimethylsilyl)-5-fluorouracil prepared from 5-fluorouracil (10 g) as in Example 1. To the mixture was added dropwise a solution of anhydrous stannic chloride (6 ml) in chloroform (15 ml) over one hour under cooling in an ice bath followed by stirring at room temperature for one hour. The reaction mixture was poured into methanol (100 ml) containing sodium bicarbonate (30 g), and after removing the resulting precipitate, the filtrate was evaporated under reduced pressure. The residue was dissolved in water (10 ml), purified by column chromatography with use of Amberlite XAD-4 (Rohm and Haas Co.), and treated with benzene to give 6.9 g of crystalline 1-(1-hydroxymethylpropyloxy)-methyl-5-fluorouracil.

後処理

  1. temperatureunder cooling in an ice bath
  2. customafter removing the resulting precipitate
  3. customthe filtrate was evaporated under reduced pressure
  4. dissolutionThe residue was dissolved in water (10 ml)
  5. custompurified by column chromatography with use of Amberlite XAD-4 (Rohm and Haas Co.)
  6. additiontreated with benzene

出典と根拠

ORDレコード
ord-86475d75c42945d7b6a596c5f8ea7110
出典データセット
uspto-grants-1983_11
特許番号
US04415573

反応ノート

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