Triethylamine → 3'-O-benzyl-2'-deoxy-3-(2-tetrahydrofuranyl)-5-fluorouridine

HRID 466092

反応式

HRID 466092 の反応式
[CH2:1]([O:8][C@@H:9]1[C@@H:13]([CH2:14][OH:15])[O:12][C@@H:11]([N:16]2[CH:23]=[C:22]([F:24])[C:20](=[O:21])[NH:19][C:17]2=[O:18])[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O[CH:29]1[CH2:33][CH2:32][CH2:31][O:30]1)(=O)C.C(N(CC)CC)C>ClCCl>[CH2:1]([O:8][C@@H:9]1[C@@H:13]([CH2:14][OH:15])[O:12][C@@H:11]([N:16]2[CH:23]=[C:22]([F:24])[C:20](=[O:21])[N:19]([CH:29]3[CH2:33][CH2:32][CH2:31][O:30]3)[C:17]2=[O:18])[CH2:10]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 102657Tetrahydro-2-furyl acetateHCID 10664574Uridine, 2'-deoxy-5-fluoro-3'-O-(phenylmethyl)-

生成物 1

HCID 137150913'-O-benzyl-2'-deoxy-3-(2-tetrahydrofuranyl)-5-fluorouridine収率 77%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

A 1.32 g quantity of N,O-bis(trimethylsiliyl)-acetamide was added with stirring to a suspension of 0.40 g of 3'-O-benzyl-2'-deoxy-5-fluorouridine in 8 ml of dry dichloromethane at room temperature. To the mixture were added, after 4 hours, 0.32 g of 2-acetoxytetrahydrofuran and a solution of 0.1 ml of stannic chloride in 1.6 ml of dry dichloromethane. The mixture was stirred for 1.5 hours and neutralized with 0.64 ml of triethylamine and washed with water. The dichloromethane layer was concentrated and the residue was dissolved in 16 ml of methanol. To the solution was added 0.24 ml of acetic acid and the mixture was left to stand for 3 hours at 40° C. The solvent was distilled off and the residue was subjected to silica gel column chromatography to conduct a gradient elution using chloroform and mixtures of methanol (up to 4%) and chloroform, giving 0.3 g of the title compound in a yield of 77%.

後処理

  1. additionTo the mixture were added, after 4 hours
  2. washwashed with water
  3. concentrationThe dichloromethane layer was concentrated
  4. dissolutionthe residue was dissolved in 16 ml of methanol
  5. additionTo the solution was added 0.24 ml of acetic acid
  6. waitthe mixture was left
  7. waitto stand for 3 hours at 40° C
  8. distillationThe solvent was distilled off
  9. washa gradient elution

出典と根拠

ORDレコード
ord-de69e7d23ed543889cc9bb5412f07d5b
出典データセット
uspto-grants-1992_10
特許番号
US05155113

関連ノート

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