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

HRID 465302

反応式

HRID 465302 の反応式
[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

参加物

5

反応物 3

HCID 8206Palmitoyl chlorideHCID 330393'-FluorothymidineHCID 21584188Chloroform methanol

生成物 1

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

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

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

後処理

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

出典と根拠

ORDレコード
ord-6d05020b4ad54e78a4feb53e3d6ecd84
出典データセット
uspto-grants-1992_10
特許番号
US05153180

関連ノート

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