Ethanol → 6-Ethoxy Abacavir

HRID 728645

반응식

HRID 728645 반응식
[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

참가 물질

4

반응물 3

HCID 702EthanolHCID 4514744-(2-Amino-6-chloro-9H-purin-9-yl)-2-cyclopentene-1-methanol, (1S,4R)-HCID 5360545Sodium2회

생성물 1

HCID 4682896-Ethoxy Abacavir수율 67.8%

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-98cb9f95e490424f9b9cf3cac312825f
출처 데이터셋
uspto-grants-1991_09
특허 번호
US05049671

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