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

HRID 1713298ノート

反応式

HRID 1713298 の反応式
[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]

参加物

5

反応物 4

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

生成物 1

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

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-64d4311f53584cfc85c9d740afb4d1a0
出典データセット
uspto-grants-2010_09
特許番号
US07795236B2

反応ノート

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