Chlorotrimethylsilane → 3'-O-benzyl-2'-deoxy-3-benzoyl-5-fluorouridine

HRID 466088ノート

反応式

HRID 466088 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[Si](C)(C)Cl.C(N(CC)CC)C.[C:37](Br)(=[O:44])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>O1CCOCC1>[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]([C:37](=[O:44])[C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=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

6

反応物 4

HCID 6397ChlorotrimethylsilaneHCID 8471Triethylamine2 回HCID 12056Benzoyl bromideHCID 10664574Uridine, 2'-deoxy-5-fluoro-3'-O-(phenylmethyl)-

生成物 1

HCID 137150613'-O-benzyl-2'-deoxy-3-benzoyl-5-fluorouridine収率 54%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

To a solution of 0.50 g of 3'-O-benzyl-2'-deoxy-5-fluorouridine in 20 ml of dioxane were added 0.75 ml of trimethylchlorosilane and 2.00 ml of triethylamine, and the mixture was stirred at room temperature for 2 hours. Then, the resulting mixture was left to stand at 60° C. for 30 minutes. To the reaction mixture were added 0.42 g of benzoyl bromide and 1.00 ml of triethylamine, and the mixture was left to stand at 60° C. for 1 hour. The solvent was distilled off and the residue was dissolved in 50 ml of ethyl acetate. Then, the solution was washed with saturated aqueous solution of sodium chloride. The ethyl acetate layer was separated and concentrated. The residue was dissolved in 30 ml of methanol and 0.5 ml of acetic acid was added thereto. The mixture was left to stand overnight. The solvent was distilled off and the residue was applied to a silica gel column to conduct gradient elution using chloroform and mixtures of methanol (up to 2%) and chloroform, giving 0.35 g of the title compound as a powder in a yield of 54%.

後処理

  1. waitThen, the resulting mixture was left
  2. waitto stand at 60° C. for 30 minutes
  3. waitthe mixture was left
  4. waitto stand at 60° C. for 1 hour
  5. distillationThe solvent was distilled off
  6. dissolutionthe residue was dissolved in 50 ml of ethyl acetate
  7. washThen, the solution was washed with saturated aqueous solution of sodium chloride
  8. customThe ethyl acetate layer was separated
  9. concentrationconcentrated
  10. dissolutionThe residue was dissolved in 30 ml of methanol
  11. addition0.5 ml of acetic acid was added
  12. waitThe mixture was left
  13. waitto stand overnight
  14. distillationThe solvent was distilled off
  15. washelution

出典と根拠

ORDレコード
ord-7f7e4ddbf85541019e3aa15dd7257b95
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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