5'-Amino-2',5'-dideoxy-5-ethyluridine → 2-(2,6-Dichloro-phenyl)-N-[(2R,3S,5R)-5-(5-ethyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl]-acetamide

HRID 232345

反応式

HRID 232345 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH2:9][C:10](Cl)=[O:11].[NH2:13][CH2:14][C@H:15]1[O:19][C@@H:18]([N:20]2[CH:27]=[C:26]([CH2:28][CH3:29])[C:24](=[O:25])[NH:23][C:21]2=[O:22])[CH2:17][C@@H:16]1[OH:30]>C(OCC)C.[OH-].[Na+]>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH2:9][C:10]([NH:13][CH2:14][C@H:15]1[O:19][C@@H:18]([N:20]2[CH:27]=[C:26]([CH2:28][CH3:29])[C:24](=[O:25])[NH:23][C:21]2=[O:22])[CH2:17][C@@H:16]1[OH:30])=[O:11]

参加物

5

反応物 2

HCID 4518285'-Amino-2',5'-dideoxy-5-ethyluridineHCID 27581482-(2,6-Dichlorophenyl)acetyl chloride

生成物 1

HCID 186334402-(2,6-Dichloro-phenyl)-N-[(2R,3S,5R)-5-(5-ethyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl]-acetamide収率 69.3%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 14798Sodium Hydroxide溶媒

実験手順

A solution of 1.12 g of (2,6-dichlorophenyl)acetyl chloride in 15 ml of diethyl ether was added to a solution of 1.275 g of 5'-amino-2',5'dideoxy-5-ethyluridine in 15 ml of 0.33M sodium hydroxide solution. The mixture was shaken vigorously for 10 minutes and then filtered. The solid was washed with 150 ml of water, 20 ml of ethanol and 40 ml of diethyl ether, and then recrystallized from 2.5 l of ethanol to give 1.53 g of 5'-[2-(2,6-dichlorophenyl)acetamido]-2',5'-dideoxy-5-ethyluridine in the form of a white solid of melting point 296°-297° C.

後処理

  1. filtrationfiltered
  2. washThe solid was washed with 150 ml of water, 20 ml of ethanol and 40 ml of diethyl ether
  3. customrecrystallized from 2.5 l of ethanol

出典と根拠

ORDレコード
ord-07923526759d4e859286abd5022bffc5
出典データセット
uspto-grants-1989_07
特許番号
US04851519

関連ノート

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