Cyclohexene → Doxifluridine

HRID 1358067

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HRID 1358067 반응식
I[CH2:2][C@H:3]1[O:7][C@@H:6]([N:8]2[CH:15]=[C:14]([F:16])[C:12](=[O:13])[NH:11][C:9]2=[O:10])[C@H:5]([OH:17])[C@@H:4]1[OH:18].C1CCCCC=1.C(N(CC)CC)C>C(O)CCC.[Pd]>[F:16][C:14]1[C:12](=[O:13])[NH:11][C:9](=[O:10])[N:8]([CH:15]=1)[C@@H:6]1[O:7][C@H:3]([CH3:2])[C@@H:4]([OH:18])[C@H:5]1[OH:17]

참가 물질

6

반응물 3

HCID 8079CyclohexeneHCID 8471TriethylamineHCID 108723875'-Deoxy-5'-iodo-5-fluorouridine

생성물 1

HCID 18343Doxifluridine수율 68%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 2631-Butanol용매

반응 조건

온도
60 °C

실험 절차

To a suspension of 10 g (0.026 m) of 5′-deoxy-5′-iodo-5-fluoro uridine, obtained as described in Example 2, step A, in 100 ml of n-butanol, 6 ml of cyclohexene (0.06 m) and 14 ml (0.1 m) of triethylamine are added. The mixture is heated to 60° C. in order to achieve a complete solubilization, then 1.5 g of 5% Pd/C are added thereinto. The suspension is heated at 80° C. for 5 hours, filtered at the same temperature by washing with hot n-butanol and concentrated under vacuum until a residue is obtained, which crystallizes with a mixture of 60 ml of ethanol and 40 ml of isopropanol. Thus, 4.5 g of 5′-deoxy-5-fluorouridine are obtained. M.p.=188÷189° C., purity (HPLC)=99.87% and [α]D=18.35° (c=0.42, H2O).

후처리

  1. customobtained
  2. temperatureThe suspension is heated at 80° C. for 5 hours
  3. filtrationfiltered at the same temperature
  4. washby washing with hot n-butanol
  5. concentrationconcentrated under vacuum until a residue
  6. customis obtained
  7. customwhich crystallizes with a mixture of 60 ml of ethanol and 40 ml of isopropanol

출처 및 근거

ORD 기록
ord-20df3c7ac38f4c0db877ff53742f7da8
출처 데이터셋
uspto-grants-2003_07
특허 번호
US06593467B2

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