Dimethylformamide → 2',3',5'-Tris-O-(tert-butyldimethylsilyl)-8-(3'-methoxy-carbonylmethoxybiphenyl-4-ylmethylamino)adenosine

HRID 1713298노트

반응식

HRID 1713298 반응식
[Si:1]([O:8][C@@H:9]1[C@H:13]([O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16])[C@@H:12]([CH2:22][O:23][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25])[O:11][C@H:10]1[N:31]1[C:40]2[N:39]=[CH:38][N:37]=[C:35]([NH2:36])[C:34]=2[N:33]=[C:32]1[NH:41][CH2:42][C:43]1[CH:48]=[CH:47][C:46]([C:49]2[CH:54]=[CH:53][CH:52]=[C:51]([OH:55])[CH:50]=2)=[CH:45][CH:44]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C:56](=[O:59])([O-])[O-].[K+].[K+].BrC[C:64](OC)=[O:65].[CH3:68]N(C)C=O>>[Si:1]([O:8][C@@H:9]1[C@H:13]([O:14][Si:15]([C:18]([CH3:19])([CH3:20])[CH3:21])([CH3:17])[CH3:16])[C@@H:12]([CH2:22][O:23][Si:24]([C:27]([CH3:28])([CH3:29])[CH3:30])([CH3:25])[CH3:26])[O:11][C@H:10]1[N:31]1[C:40]2[N:39]=[CH:38][N:37]=[C:35]([NH2:36])[C:34]=2[N:33]=[C:32]1[N:41]([O:65][CH:64]=[C:56]=[O:59])[CH2:42][C:43]1[CH:44]=[CH:45][C:46]([C:49]2[CH:54]=[CH:53][CH:52]=[C:51]([O:55][CH3:68])[CH:50]=2)=[CH:47][CH:48]=1)([C:4]([CH3:6])([CH3:7])[CH3:5])([CH3:2])[CH3:3]

참가 물질

5

반응물 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 674557002',3',5'-Tris-o-(tert-butyl-dimethylsilyl)-8-(3'-hydroxybiphenyl-4-ylmethylamino)-adenosine

생성물 1

HCID 1317283222',3',5'-Tris-O-(tert-butyldimethylsilyl)-8-(3'-methoxy-carbonylmethoxybiphenyl-4-ylmethylamino)adenosine

실험 절차

To a solution of 2′,3′,5′-tris-O-(tert-butyl-dimethylsilyl)-8-(3′-hydroxybiphenyl-4-ylmethylamino)-adenosine (0.612 g) in N,N-dimethylformamide (4.0 mL) was added potassium carbonate (0.165 g). Then methyl bromoacetate (0.098 mL) was added, and the resulting mixture was stirred at room temperature for 5 hours. The reaction mixture was partitioned between diethyl ether (55 mL) and water (10 mL). The organic layer was washed successively with water (10 mL×2) and brine (10 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=3/2) to give the title compound (0.423 g).

후처리

  1. customThe reaction mixture was partitioned between diethyl ether (55 mL) and water (10 mL)
  2. washThe organic layer was washed successively with water (10 mL×2) and brine (10 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=3/2)

출처 및 근거

ORD 기록
ord-64d4311f53584cfc85c9d740afb4d1a0
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07795236B2

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