Carbon Dioxide → 3-Hydroxy-2-(hydroxymethyl)-2,3,3a,9a-tetrahydro-6H-furo[2',3':4,5][1,3]oxazolo[3,2-a]pyrimidin-6-one

HRID 1086146ノート

反応式

HRID 1086146 の反応式
[C@@H:1]1([N:10]2[CH:17]=[CH:16][C:14](=[O:15])[NH:13][C:11]2=[O:12])[O:9][C@H:6]([CH2:7][OH:8])[C@@H:4]([OH:5])[C@H:2]1O.CN(C)C=O.C1(OC(=O)OC2C=CC=CC=2)C=CC=CC=1.C(=O)=O>C(=O)(O)[O-].[Na+].CCOCC>[CH:16]1[C:14](=[O:15])[N:13]=[C:11]2[N:10]([CH:1]3[O:9][CH:6]([CH2:7][OH:8])[CH:4]([OH:5])[CH:2]3[O:12]2)[CH:17]=1

参加物

7

反応物 4

HCID 280Carbon DioxideHCID 6029UridineHCID 6228DimethylformamideHCID 7597Diphenyl carbonate

生成物 1

HCID 989613-Hydroxy-2-(hydroxymethyl)-2,3,3a,9a-tetrahydro-6H-furo[2',3':4,5][1,3]oxazolo[3,2-a]pyrimidin-6-one収率 80%

試薬・触媒・溶媒 2

HCID 516892Sodium Bicarbonate触媒HCID 3283Diethyl Ether溶媒

実験手順

Uridine (10 g, 0.04 mole) was dissolved in 20 ml of warm, dry dimethylformamide, and 11.4 g of diphenylcarbonate (0.06 m) and 0.2 g of sodium bicarbonate were added. The solution was stirred and heated at 150° C. until evolution of carbon dioxide ceased (30 min approx). After cooling the solution was poured into 200 ml of ether with rapid stirring. The resulting solid was filtered off, washed with ether, and recrystallised from methanol to give 7.2 g (80%) of the title compound, as white crystals, melting at 235°-40° C.

後処理

  1. temperatureof warm
  2. custom(30 min approx)
  3. temperatureAfter cooling the solution
  4. filtrationThe resulting solid was filtered off
  5. washwashed with ether
  6. customrecrystallised from methanol

出典と根拠

ORDレコード
ord-bbfb7ccb6d8d4097b9633dcd7c1c7d16
出典データセット
uspto-grants-1991_07
特許番号
US05028596

反応ノート

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