Ethanol → 6-Ethoxy Abacavir

HRID 728645

Reaction equation

HRID 728645 reaction equation
[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

Participants

4

Reactant 3

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

Product 1

HCID 4682896-Ethoxy AbacavirYield 67.8%

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-98cb9f95e490424f9b9cf3cac312825f
Source dataset
uspto-grants-1991_09
Patent number
US05049671

Linked notes

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