Triethylamine → 3-benzoyl-2'-deoxy-3',5'-di-O-acetyl-5-fluorouridine

HRID 745656ノート

反応式

HRID 745656 の反応式
[C:1]([O:4][C@@H:5]1[C@@H:9]([CH2:10][O:11][C:12](=[O:14])[CH3:13])[O:8][C@@H:7]([N:15]2[CH:22]=[C:21]([F:23])[C:19](=[O:20])[NH:18][C:16]2=[O:17])[CH2:6]1)(=[O:3])[CH3:2].C(N(CC)CC)C.[C:31](Br)(=[O:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>O1CCOCC1>[C:31]([N:18]1[C:19](=[O:20])[C:21]([F:23])=[CH:22][N:15]([C@@H:7]2[O:8][C@H:9]([CH2:10][O:11][C:12](=[O:14])[CH3:13])[C@@H:5]([O:4][C:1](=[O:3])[CH3:2])[CH2:6]2)[C:16]1=[O:17])(=[O:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 12056Benzoyl bromideHCID 127901643',5'-Di-O-acetyl-2'-deoxy-5-fluorouridine

生成物 1

HCID 228287873-benzoyl-2'-deoxy-3',5'-di-O-acetyl-5-fluorouridine収率 60.8%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

500 mg of 2'-deoxy-3',5'-di-O-acetyl-5-fluorouridine and 0.76 ml of triethylamine were dissolved in 10 ml of dry dioxane, and the resulting mixture was cooled with ice. To the mixture was added 850 mg of benzoyl bromide, and the resulting mixture was allowed to stand at room temperature for 15 minutes and then at 70° C. for 30 minutes. The same procedure as in Example 8 gave 400 mg (yield: 60.5%) of 3-benzoyl-2'-deoxy-3',5'-di-O-acetyl-5-fluorouridine. The absorption spectra of the present product were identical with those of the compound obtained in Example 8.

後処理

  1. temperaturethe resulting mixture was cooled with ice
  2. waitat 70° C. for 30 minutes

出典と根拠

ORDレコード
ord-df7060b2176247bf92466a52c925e2b9
出典データセット
uspto-grants-1986_07
特許番号
US04599404

反応ノート

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