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

HRID 895273

반응식

HRID 895273 반응식
[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(OCC)(=O)C.CO>[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

참가 물질

8

반응물 5

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

생성물 1

HCID 100028392'-o-Phthalimidoethyl-5-methyluridine

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 21584119Ethylacetate methanol용매

반응 조건

온도
150 °C

실험 절차

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 gas evolution 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 and placed in an oil bath and heated to 150° C. internal temperature for 24 h. The bomb was cooled to room temperature and opened. TLC (ethyl acetate-methanol; 95:5) revealed the disappearance of starting material. The crude solution was concentrated and the residue was purified by chromatography on silica gel starting with ethyl acetate to remove the excess phthalimide reagent, followed by ethyl acetate-methanol (95:5) to elute 2 (22.2 g, 20.6%).

후처리

  1. dissolutiondissolved
  2. customthe bomb was sealed
  3. customplaced in an oil bath
  4. temperatureThe bomb was cooled to room temperature
  5. concentrationThe crude solution was concentrated
  6. customthe residue was purified by chromatography on silica gel starting with ethyl acetate
  7. customto remove the excess phthalimide reagent
  8. washto elute 2 (22.2 g, 20.6%)

출처 및 근거

ORD 기록
ord-68def3d70d674509bda6cfce76cf84a2
출처 데이터셋
uspto-grants-2005_07
특허 번호
US06914148B2

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