Borane → 2'-o-Phthalimidoethyl-5-methyluridine

HRID 1250000

反応式

HRID 1250000 の反応式
[OH:1][CH2:2][CH2:3][N:4]1[C:8](=[O:9])[C:7]2=[CH:10][CH:11]=[CH:12][CH:13]=[C:6]2[C:5]1=[O:14].B.[H][H].[CH3:18][C:19]1[C:33](=[O:34])[N:32]=[C:31]2[N:21]([C@@H:22]3[O:26][C@H:25]([CH2:27][OH:28])[C@@H:24]([OH:29])[C@@H:23]3[O:30]2)[CH:20]=1.C(=O)(O)[O-].[Na+]>O1CCCC1>[C:8]1(=[O:9])[N:4]([CH2:3][CH2:2][O:1][C@@H:23]2[C@H:24]([OH:29])[C@@H:25]([CH2:27][OH:28])[O:26][C@H:22]2[N:21]2[CH:20]=[C:19]([CH3:18])[C:33](=[O:34])[NH:32][C:31]2=[O:30])[C:5](=[O:14])[C:6]2=[CH:13][CH:12]=[CH:11][CH:10]=[C:7]12

参加物

7

反応物 5

HCID 6331BoraneHCID 77499N-(2-Hydroxyethyl)phthalimideHCID 1680452,2'-Anhydro-1-beta-arabinofuranosylthymineHCID 516892Sodium BicarbonateHCID 178418361HCID 178418361、化合物

生成物 1

HCID 100028392'-o-Phthalimidoethyl-5-methyluridine収率 90%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
150 °C

実験手順

N-(2-Hydroxyethyl)phthalimide (277 g, 1.45 mol) was slowly added to a solution of borane in tetrahydrofuran (1 M, 600 mL) with stirring. Hydrogen gas evolved as the solid dissolved. Once the rate of bubbling subsided, the solution was placed in a 2 L stainless steel bomb. 2,2′-anhydro-5-methyluridine (60 g, 0.25 mol) and sodium bicarbonate (120 mg) were added and the bomb was sealed. After 30 minutes, the bomb was vented for the last time and then placed in an oil bath and heated to 150° C. internal temperature for 24 hours. The bomb was cooled to room temperature and opened. TLC revealed all the starting material was gone. The crude solution was concentrated and the residue was columned on silica gel starting with straight ethyl acetate to remove the excess phthalimide reagent followed by ethyl acetate-methanol 95/5 to elute the product to give 22.2 g (20.6%) of ca 90% pure product.

後処理

  1. dissolutiondissolved
  2. customOnce the rate of bubbling
  3. customthe bomb was sealed
  4. customplaced in an oil bath
  5. temperatureThe bomb was cooled to room temperature
  6. concentrationThe crude solution was concentrated
  7. customto remove the excess phthalimide reagent
  8. washto elute the product

出典と根拠

ORDレコード
ord-d9c4b76605064fd0b929d8fdbe98ba41
出典データセット
uspto-grants-2002_01
特許番号
US06335437B1

関連ノート

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