Triethylamine → 5'-O-acetyl-3-(4-chlorobenzoyl)-3'-O-(4-chlorobenzyl)-2'-deoxy-5-fluorouridine

HRID 466098ノート

反応式

HRID 466098 の反応式
[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][O:7][C@@H:8]2[C@@H:12]([CH2:13][O:14][C:15](=[O:17])[CH3:16])[O:11][C@@H:10]([N:18]3[CH:25]=[C:24]([F:26])[C:22](=[O:23])[NH:21][C:19]3=[O:20])[CH2:9]2)=[CH:4][CH:3]=1.[Cl:29][C:30]1[CH:38]=[CH:37][C:33]([C:34](Cl)=[O:35])=[CH:32][CH:31]=1.C(N(CC)CC)C>O1CCOCC1>[C:15]([O:14][CH2:13][C@H:12]1[O:11][C@@H:10]([N:18]2[CH:25]=[C:24]([F:26])[C:22](=[O:23])[N:21]([C:34](=[O:35])[C:33]3[CH:37]=[CH:38][C:30]([Cl:29])=[CH:31][CH:32]=3)[C:19]2=[O:20])[CH2:9][C@@H:8]1[O:7][CH2:6][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:28][CH:27]=1)(=[O:17])[CH3:16]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 85014-Chlorobenzoyl chlorideHCID 13715059HCID 13715059、化合物

生成物 1

HCID 137151005'-O-acetyl-3-(4-chlorobenzoyl)-3'-O-(4-chlorobenzyl)-2'-deoxy-5-fluorouridine収率 82.4%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
40 °C

実験手順

To a solution of 0.30 g of 3'-O-(4-chlorobenzyl)-5'-O-acetyl-2'-deoxy-5-fluorouridine in 30 ml of dioxane were added 0.38 g of 4-chlorobenzoyl chloride and 0.61 ml of triethylamine, and the mixture was stirred at 40° C. for 3 hours. The insolubles were removed by filtration, and the residue was dissolved in 50 ml of ethyl acetate. The solution was washed with water and dried. The ethyl acetate was distilled off, and the residue was placed on a silica gel column and eluted with chloroform-n-hexane (3:2), thereby producing 0.33 g of the title compound in a yield of 82%.

後処理

  1. customThe insolubles were removed by filtration
  2. dissolutionthe residue was dissolved in 50 ml of ethyl acetate
  3. washThe solution was washed with water
  4. customdried
  5. distillationThe ethyl acetate was distilled off
  6. washeluted with chloroform-n-hexane (3:2)

出典と根拠

ORDレコード
ord-4592c04c83384e83ae339a2d7a7436dc
出典データセット
uspto-grants-1992_10
特許番号
US05155113

反応ノート

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