Potassium Hydroxide → HCID 15124909, 화합물

HRID 981733

반응식

HRID 981733 반응식
[F:1][C:2]1[C:3](=[O:36])[NH:4][C:5](=[O:35])[N:6]([CH:34]=1)[C@@H:7]1[O:33][C@H:11]([CH2:12][O:13]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[C@@H:9]([OH:10])[CH2:8]1.[OH-].[K+].[Br:39][C:40]1[S:41][C:42]([CH2:47]Cl)=[C:43]([Br:46])[C:44]=1[Br:45]>O1CCOCC1>[F:1][C:2]1[C:3](=[O:36])[NH:4][C:5](=[O:35])[N:6]([CH:34]=1)[C@@H:7]1[O:33][C@H:11]([CH2:12][OH:13])[C@@H:9]([O:10][CH2:47][C:42]2[S:41][C:40]([Br:39])=[C:44]([Br:45])[C:43]=2[Br:46])[CH2:8]1

참가 물질

5

반응물 3

HCID 14797Potassium HydroxideHCID 108387042'-deoxy-5'-O-trityl-5-fluorouridineHCID 151249082,3,4-Tribromo-5-(chloromethyl)thiophene

생성물 1

HCID 15124909HCID 15124909, 화합물수율 18.1%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

반응 조건

온도
80 °C

실험 절차

To a solution of 5.00 g of 2'-deoxy-5-fluoro-5'-O-trityluridine in 100 ml of dioxane were added 5.74 g of fine powder of potassium hydroxide and 5.65 g of 2,3,4- tribromo-5-chloromethylthiophene, and the mixture was stirred at a temperature of 80° C. for 2 hours. The reaction mixture was concentrated and the residue was dissolved in 100 ml of ethyl acetate. The solution was washed with aqueous solution of acetic acid, dried and concentrated. To the residue was added 100 ml of 80% acetic acid and the mixture was left to stand at a temperature of 80° C. for one hour. The solvent was distilled off and the residue was placed on silica gel column and eluted with 2% methanol-chloroform for purification, giving 1.07 g (18%) of the desired 2'-deoxy 5-fluoro-3'-O-(3,4,5-tribromo-2-thenyl)uridine.

후처리

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe residue was dissolved in 100 ml of ethyl acetate
  3. washThe solution was washed with aqueous solution of acetic acid
  4. customdried
  5. concentrationconcentrated
  6. additionTo the residue was added 100 ml of 80% acetic acid
  7. waitthe mixture was left
  8. waitto stand at a temperature of 80° C. for one hour
  9. distillationThe solvent was distilled off
  10. washeluted with 2% methanol-chloroform for purification

출처 및 근거

ORD 기록
ord-b804364ba17d4ef4a3b26b125af93c3a
출처 데이터셋
uspto-grants-1991_02
특허 번호
US04992534

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