Tetrahydrofuran → Sonedenoson

HRID 1392016노트

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HRID 1392016 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][O:10][C:11]2[N:12]=[C:13]([NH2:50])[C:14]3[N:15]=[CH:16][N:17]([C:48]=3[N:49]=2)[C@@H:18]2[O:47][C@H:37]([CH2:38][O:39][Si](C(C)(C)C)(C)C)[C@@H:28]([O:29][Si](C(C)(C)C)(C)C)[C@H:19]2[O:20][Si](C(C)(C)C)(C)C)=[CH:4][CH:3]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-].C1COCC1>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][O:10][C:11]2[N:12]=[C:13]([NH2:50])[C:14]3[N:15]=[CH:16][N:17]([C:48]=3[N:49]=2)[C@@H:18]2[O:47][C@H:37]([CH2:38][OH:39])[C@@H:28]([OH:29])[C@H:19]2[OH:20])=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 156063272-[2-(4-Chlorophenyl)ethoxy]-2',3',5'-tri-o-(tert-butyldimethylsilyl)-adenosine

생성물 1

HCID 9910098Sonedenoson수율 46.4%

시약·촉매·용매 1

HCID 887Methanol용매

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온도
50 °C

실험 절차

To a solution of 2-[2-(4-chlorophenyl)ethoxy]-2′,3′,5′-tri-O-(TERT-butyldimethylsilyl)-adenosine (Example 1, 500 mg, 0.654 mmol) in 7 mL of anhydrous methanol flushed with nitrogen was added 3.27 mL of a 1.0 M solution of TBAF in THF (5 equiv). The reaction was heated to 50° C. for 48 hours. Upon disappearance of the starting material as indicated by LC/MS analysis, the reaction mixture was allowed to cool to room temperature and was concentrated to dryness. Ethyl acetate (20 ml) and water (20 ml) were added and stirred for 5 minutes. The layers were separated and the aqueous layer reextracted with ethyl acetate (2×20 ml). The organic phases were combined, dried over MgSO4 and concentrated to give an oil. The crude material was then purified on silica gel, eluting with a gradient of 0%-10% methanol in CH2Cl2, affording 128 mg (46%) of the desired product as a white solid.

후처리

  1. temperatureto cool to room temperature
  2. concentrationwas concentrated to dryness
  3. additionEthyl acetate (20 ml) and water (20 ml) were added
  4. customThe layers were separated
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customto give an oil
  8. customThe crude material was then purified on silica gel
  9. washeluting with a gradient of 0%-10% methanol in CH2Cl2

출처 및 근거

ORD 기록
ord-fc7e6c8f3b4c485ab4bdc9abd56a676e
출처 데이터셋
uspto-grants-2008_03
특허 번호
US07342003B2

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