5-Fluorouracil → 1-[alpha-(2-Hydroxyethoxy)-2-acetoxybenzyl]-5-fluorouracil

HRID 1649111ノート

反応式

HRID 1649111 の反応式
[C:1]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH:11]1[O:15][CH2:14][CH2:13][O:12]1)(=[O:3])[CH3:2].[F:16][C:17]1[C:18](=[O:24])[NH:19][C:20](=[O:23])[NH:21][CH:22]=1>ClCCl.C[Si](C1NC(=O)N([Si](C)(C)C)C(=O)C=1F)(C)C>[OH:12][CH2:13][CH2:14][O:15][CH:11]([N:21]1[CH:22]=[C:17]([F:16])[C:18](=[O:24])[NH:19][C:20]1=[O:23])[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=1[O:4][C:1](=[O:3])[CH3:2]

参加物

5

反応物 2

HCID 33855-FluorouracilHCID 155835892-(2-Acetoxyphenyl)-1,3-dioxolan

生成物 1

HCID 155835541-[alpha-(2-Hydroxyethoxy)-2-acetoxybenzyl]-5-fluorouracil収率 16.1%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 68585259HCID 68585259、化合物溶媒

実験手順

2-Hydroxygenzaldehyde (10 g) was dissolved in acetic anhydride (30 ml) and pyridine (30 ml) followed by stirring at room temperature for 3 hours. The reaction mixture was poured into ice-water and the resulting precipitate was recovered by filtration. The precipitate was dissolved in chloroform (100 ml), washed with water, dried and evaporated to give 2-acetoxybenzaldehyde. To a solution of 2-acetoxy-benzaldehyde (13 g) and ethyleneglycol (10 ml) in benzene (80 ml) was added Amberlist 15 (Rohm and Haas Co.) (3 g) and followed by refluxing for 5 hours. Water generated during refluxing was removed as an azeotropic mixture. The reaction mixture was washed with an aqueous solution of sodium bicarbonate, and then with water, and dried and evaporated. The residue was distilled under reduced pressure to collect a fraction distilled out at 115°-125° C./4 mmHg to give 10 g of 2-(2-acetoxyphenyl)-1,3-dioxolan. To a solution of 2-(2-acetoxy-phenyl)-1,3-dioxolan (19.6 g) in dichloromethane (50 ml), bis(trimethylsilyl)-5-fluorouracil prepared as in Example 1 from 5-fluorouracil (10 g) was added and treated as in Example 10 to give 4.2 g of crystalline 1-[α-(2-hydroxyethoxy)-2-acetoxybenzyl]-5-fluorouracil.

後処理

  1. additionwas added
  2. additiontreated as in Example 10

出典と根拠

ORDレコード
ord-5d64c1ddeb9a4c01b69de0e29c9ca076
出典データセット
uspto-grants-1983_11
特許番号
US04415573

反応ノート

読み込み中…