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

HRID 1649106노트

반응식

HRID 1649106 반응식
[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]

참가 물질

8

반응물 5

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

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 6212Chloroform용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-86475d75c42945d7b6a596c5f8ea7110
출처 데이터셋
uspto-grants-1983_11
특허 번호
US04415573

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