Palmitoyl chloride → 3'-deoxy-3'-fluoro-5'-O-palmitoyl-thymidine

HRID 1088909

반응식

HRID 1088909 반응식
[C:1](Cl)(=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[F:19][C@@H:20]1[C@@H:24]([CH2:25][OH:26])[O:23][C@@H:22]([N:27]2[CH:35]=[C:33]([CH3:34])[C:31](=[O:32])[NH:30][C:28]2=[O:29])[CH2:21]1.C(Cl)(Cl)Cl.CO>N1C=CC=CC=1>[F:19][C@@H:20]1[C@@H:24]([CH2:25][O:26][C:1](=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[O:23][C@@H:22]([N:27]2[CH:35]=[C:33]([CH3:34])[C:31](=[O:32])[NH:30][C:28]2=[O:29])[CH2:21]1

참가 물질

5

반응물 3

HCID 8206Palmitoyl chlorideHCID 330393'-FluorothymidineHCID 21584188Chloroform methanol

생성물 1

HCID 152283303'-deoxy-3'-fluoro-5'-O-palmitoyl-thymidine

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

At 0° C., 1.2 equivalents of palmitoyl chloride were added to a solution of 3'-deoxy-3'-fluorothymidine in pyridine. The solution was warmed slowly to room temperature. As soon as a thin layer chromatographic control (CHCl3 /methanol=95/5 on silica gel) showed a complete reaction, the solution was poured into ice water. The aqueous phase was decanted, the resulting oil was chromatographed on silica gel with chloroform eluent. The title compound was recovered from the suitable fractions by evaporation of the solvent. M.P. 65°-66° C. (cyclohexane).

후처리

  1. customa complete reaction
  2. customThe aqueous phase was decanted
  3. customthe resulting oil was chromatographed on silica gel with chloroform eluent
  4. customThe title compound was recovered from the suitable fractions by evaporation of the solvent

출처 및 근거

ORD 기록
ord-3deb81ccc9e241bb87d8dc9f1e866483
출처 데이터셋
uspto-grants-1990_10
특허 번호
US04963662

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