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

HRID 1713298Notes

Reaction equation

HRID 1713298 reaction equation
[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]

Participants

5

Reactant 4

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

Product 1

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

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-64d4311f53584cfc85c9d740afb4d1a0
Source dataset
uspto-grants-2010_09
Patent number
US07795236B2

Reaction notes

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