Methanol → HCID 136378402, compound

HRID 1110060Notes

Reaction equation

HRID 1110060 reaction equation
[N:1]#[N:2].[CH3:3][O:4][C:5]1[CH:70]=[CH:69][C:8]([C:9]([NH:24][C:25]2[NH:26][C:27](=[O:68])[C:28]3[N:29]=[CH:30][N:31]([C@@H:34]4[CH2:37][C@H:36]([CH2:38][O:39]C(=O)C)[C@H:35]4[CH2:43][O:44][C:45]([C:62]4[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=4)([C:54]4[CH:59]=[CH:58][C:57]([O:60][CH3:61])=[CH:56][CH:55]=4)[C:46]4[CH:51]=[CH:50][C:49]([O:52][CH3:53])=[CH:48][CH:47]=4)[C:32]=3[N:33]=2)([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)=[CH:7][CH:6]=1.CO.C(=O)([O-])[O-].[K+].[K+].P([O-])([O-])([O-])=O>C(Cl)Cl>[N:1]#[N:2].[CH3:17][O:16][C:13]1[CH:14]=[CH:15][C:10]([C:9]([NH:24][C:25]2[NH:26][C:27](=[O:68])[C:28]3[N:29]=[CH:30][N:31]([C@@H:34]4[CH2:37][C@H:36]([CH2:38][OH:39])[C@H:35]4[CH2:43][O:44][C:45]([C:62]4[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=4)([C:54]4[CH:55]=[CH:56][C:57]([O:60][CH3:61])=[CH:58][CH:59]=4)[C:46]4[CH:51]=[CH:50][C:49]([O:52][CH3:53])=[CH:48][CH:47]=4)[C:32]=3[N:33]=2)([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:8]2[CH:7]=[CH:6][C:5]([O:4][CH3:3])=[CH:70][CH:69]=2)=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 1061PhosphateHCID 11430Potassium CarbonateHCID 136378404HCID 136378404, compound

Product 1

HCID 136378402HCID 136378402, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The N2 -(4,4'-dimethoxytrityl)-9-[(1R,2R,3S)-2-(4,4'-dimethoxytrity)oxymethyl-3-acetoxymethyl-1-cyclobutyl]-guanine (447 mg, 0.49 mmole) obtained above is dissolved into a mixture consisting of methanol (5 ml) and methylene chloride (1 ml), potassium carbonate (76 mg, 0.55 mmole) is added under cooling with ice, and the mixture is stirred at room temperature overnight. After adding 0.2M phosphate buffer to the reaction mixture, it is extracted with ethyl acetate. The extract solution is washed with saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate, and the solvent is distilled off under reduced pressure. The residue is purified by silica gel column chromatography (methylene chloride:methanol=30:1) to obtain N2 -(4,4'-dimethoxytrityl)-9-[(1R,2R,3S)-2-(4,4'-dimethoxytrityl)oxymethyl-3-hydroxymethyl-1-cyclobutyl]-guanine (364 mg, 85%).

Workup

  1. dissolutionabove is dissolved into a mixture
  2. additionis added
  3. temperatureunder cooling with ice
  4. extractionis extracted with ethyl acetate
  5. washThe extract solution is washed with saturated aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationthe solvent is distilled off under reduced pressure
  8. customThe residue is purified by silica gel column chromatography (methylene chloride:methanol=30:1)

Sources & evidence

ORD record
ord-ad8481b2ca084541995f07632553b926
Source dataset
uspto-grants-1994_06
Patent number
US05324730

Reaction notes

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