2-Hydrazinoadenosine → Ethyl 1-(6-amino-9-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-9H-purin-2-yl)-1H-pyrazole-4-carboxylate

HRID 15293

反応式

HRID 15293 の反応式
[CH:1]([CH:3]([CH:9]=O)[C:4]([O:6][CH2:7][CH3:8])=[O:5])=O.[NH:11]([C:13]1[N:14]=[C:15]([NH2:31])[C:16]2[N:17]=[CH:18][N:19]([C:29]=2[N:30]=1)[C@@H:20]1[O:28][C@H:25]([CH2:26][OH:27])[C@@H:23]([OH:24])[C@H:21]1[OH:22])[NH2:12]>CC(O)C>[OH:22][C@@H:21]1[C@H:23]([OH:24])[C@@H:25]([CH2:26][OH:27])[O:28][C@H:20]1[N:19]1[CH:18]=[N:17][C:16]2[C:29]1=[N:30][C:13]([N:11]1[CH:1]=[C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH:9]=[N:12]1)=[N:14][C:15]=2[NH2:31]

参加物

4

反応物 2

HCID 103572622-HydrazinoadenosineHCID 11029955Ethyl 2-formyl-3-oxopropanoate

生成物 1

HCID 9865974Ethyl 1-(6-amino-9-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-9H-purin-2-yl)-1H-pyrazole-4-carboxylate

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

実験手順

Ethyl 2-formyl-3-oxopropionate (23.93 g, 0.17 mol) was placed in a flask equipped with mechanical stirrer, gas inlet, gas outlet and reflux condenser. 2-Propanol was added to the flask followed by 2-hydrazinoadenosine (44.45 g, 0.15 mol). The mixture was heated to reflux under stirring for 2-4 hours, following the progress of the reaction by TLC analysis. When the reaction was judged complete, the heat source was removed and the mixture cooled to room temperature. The suspension was cooled under stirring in an ice-bath for 1.5 to 2 hours. The solids were isolated by vacuum filtration, and washed with ice-cold 2-propanol. The product, ethyl 1-{9-[(4S,2R,3R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-aminopurin-2-yl}pyrazole-4-carboxylate, was dried under reduced pressure to a constant weight. Yield 54.29 g, purity (by HPLC) 96.6%.

後処理

  1. customequipped with mechanical stirrer, gas inlet, gas outlet
  2. temperaturereflux condenser
  3. temperatureThe mixture was heated
  4. temperatureto reflux
  5. customthe progress of the reaction by TLC analysis
  6. customthe heat source was removed
  7. temperatureThe suspension was cooled
  8. stirringunder stirring in an ice-bath for 1.5 to 2 hours
  9. customThe solids were isolated by vacuum filtration
  10. washwashed with ice-cold 2-propanol
  11. dry with materialThe product, ethyl 1-{9-[(4S,2R,3R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-aminopurin-2-yl}pyrazole-4-carboxylate, was dried under reduced pressure to a constant weight

出典と根拠

ORDレコード
ord-54710e3bffb648aeb2702ca8766ff199
出典データセット
uspto-grants-2010_06
特許番号
US07732595B2

関連ノート

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