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

HRID 1088909

反応式

HRID 1088909 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 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).

後処理

  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

出典と根拠

ORDレコード
ord-3deb81ccc9e241bb87d8dc9f1e866483
出典データセット
uspto-grants-1990_10
特許番号
US04963662

関連ノート

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