Ethanol → 6-Ethoxy Abacavir

HRID 728645

反応式

HRID 728645 の反応式
[Na].[NH2:2][C:3]1[N:11]=[C:10]2[C:6]([N:7]=[CH:8][N:9]2[C@@H:12]2[CH2:16][C@H:15]([CH2:17][OH:18])[CH:14]=[CH:13]2)=[C:5](Cl)[N:4]=1.[CH2:20]([OH:22])[CH3:21]>>[NH2:2][C:3]1[N:11]=[C:10]2[C:6]([N:7]=[CH:8][N:9]2[C@@H:12]2[CH2:16][C@H:15]([CH2:17][OH:18])[CH:14]=[CH:13]2)=[C:5]([O:22][CH2:20][CH3:21])[N:4]=1

参加物

4

反応物 3

HCID 702EthanolHCID 4514744-(2-Amino-6-chloro-9H-purin-9-yl)-2-cyclopentene-1-methanol, (1S,4R)-HCID 5360545Sodium2 回

生成物 1

HCID 4682896-Ethoxy Abacavir収率 67.8%

実験手順

A flask was charged with ethanol (33 ml) and sodium (0.172 g, 7.5 mmol). After all of the sodium had dissolved (±)-cis-4-(2-amino-6-chloro-9H-purin-9-yl)-2-cyclopentene-1-methanol (0.40 g, 1.5 mmol) from Example 4 was added and the solution was brought to reflux for 0.5 hours. The solution was allowed to cool to room temperature before neutralization with 1.0 N HC1. The solution was then concentrated and the residue partitioned between chloroform and water. The organic layer was dried with MgSO4, filtered and concentrated. The residues were then placed on a silica gel column and eluted with 2% methanol in chloroform to yield a yellow glass (0.28 g, 67.8%).

後処理

  1. additionwas added
  2. temperatureto reflux for 0.5 hours
  3. concentrationThe solution was then concentrated
  4. customthe residue partitioned between chloroform and water
  5. dry with materialThe organic layer was dried with MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. washeluted with 2% methanol in chloroform

出典と根拠

ORDレコード
ord-98cb9f95e490424f9b9cf3cac312825f
出典データセット
uspto-grants-1991_09
特許番号
US05049671

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