5-Fluorouracil → 1-[1-(2-Hydroxyethoxy)propyl]-5-fluorouracil

HRID 1649105노트

반응식

HRID 1649105 반응식
C[Si]([C:5]1[NH:10][C:9](=[O:11])[N:8]([Si](C)(C)C)[C:7](=[O:16])[C:6]=1[F:17])(C)C.FC1C(=O)NC(=O)NC=1.[CH2:27]([CH:29]1[O:33][CH2:32][CH2:31][O:30]1)[CH3:28].C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl.CO.C(O)CO>[OH:33][CH2:32][CH2:31][O:30][CH:29]([N:10]1[CH:5]=[C:6]([F:17])[C:7](=[O:16])[NH:8][C:9]1=[O:11])[CH2:27][CH3:28]

참가 물질

8

반응물 4

HCID 33855-FluorouracilHCID 173812-Ethyl-1,3-dioxolaneHCID 516892Sodium BicarbonateHCID 68585259HCID 68585259, 화합물

생성물 1

HCID 130571221-[1-(2-Hydroxyethoxy)propyl]-5-fluorouracil

시약·촉매·용매 3

HCID 174Ethylene Glycol용매HCID 887Methanol용매HCID 6212Chloroform용매2회

실험 절차

Bis(trimethylsilyl)-5-fluorouracil which had been prepared by treating 5-fluorouracil (10 g) as in Example 1 was dissolved in chloroform (20 ml). Separately prepared 2-ethyl-1,3-dioxolan (15 ml) from propionyldehyde (25 ml) and ethylene glycol (25 ml) was added to the above solution. Then, to the mixture was added dropwise a solution of anhydrous stannic chloride (6 ml) in chloroform (15 ml) under cooling in an ice bath for one hour. Following 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 by filtration, 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 then treated with benzene to give 8.7 of crystalline 1-[1-(2-hydroxyethoxy)propyl]-5-fluorouracil.

후처리

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

출처 및 근거

ORD 기록
ord-ea2c0faa4d74479f85e45ecab32feb2e
출처 데이터셋
uspto-grants-1983_11
특허 번호
US04415573

반응 노트

불러오는 중…