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

반응식

HRID 232345 반응식
[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]

참가 물질

5

반응물 2

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

생성물 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]-acetamide수율 69.3%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 14798Sodium Hydroxide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-07923526759d4e859286abd5022bffc5
출처 데이터셋
uspto-grants-1989_07
특허 번호
US04851519

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