1,1'-(Chlorophenylmethylene)bis(4-methoxybenzene) → HCID 86761226, compound

HRID 2262394Notes

Reaction equation

HRID 2262394 reaction equation
[C:1]1([N:7]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:8]([O:10][C:11]2[C:12]3[N:13]=[CH:14][N:15]([C:24]=3[N:25]=[C:26]([NH:28][C:29](=[O:32])[NH:30][CH3:31])[N:27]=2)[C@@H:16]2[O:23][C@H:20]([CH2:21][OH:22])[C@@H:18]([OH:19])[CH2:17]2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:39][O:40][C:41]1[CH:62]=[CH:61][C:44]([C:45](Cl)([C:54]2[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=2)[C:46]2[CH:51]=[CH:50][C:49]([O:52][CH3:53])=[CH:48][CH:47]=2)=[CH:43][CH:42]=1>N1C=CC=CC=1>[CH3:53][O:52][C:49]1[CH:48]=[CH:47][C:46]([C:45]([O:22][CH2:21][C@H:20]2[O:23][C@@H:16]([N:15]3[C:24]4[N:25]=[C:26]([NH:28][C:29](=[O:32])[NH:30][CH3:31])[N:27]=[C:11]([O:10][C:8](=[O:9])[N:7]([C:1]5[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=5)[C:33]5[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=5)[C:12]=4[N:13]=[CH:14]3)[CH2:17][C@@H:18]2[OH:19])([C:54]2[CH:55]=[CH:56][CH:57]=[CH:58][CH:59]=2)[C:44]2[CH:61]=[CH:62][C:41]([O:40][CH3:39])=[CH:42][CH:43]=2)=[CH:51][CH:50]=1

Participants

4

Reactant 2

HCID 968311,1'-(Chlorophenylmethylene)bis(4-methoxybenzene)HCID 86761227HCID 86761227, compound

Product 1

HCID 86761226HCID 86761226, compoundYield 87.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

The thus obtained 6-O-diphenylcarbamoyl-2-N-methylcarbamoyldeoxyguanosine (643 mg, 1.24 mmol) was azeotroped with anhydrous pyridine three times and then dissolved in anhydrous pyridine (21 mL), and 4,4′-dimethoxytrityl chloride (629 mg, 1.86 mmol) was added thereto. The mixture was stirred at room temperature for 3 hours. Then, the reaction was terminated by adding sodium bicarbonate water (5 mL) thereto. The reaction solution was extracted with ethyl acetate (100 mL)/sodium bicarbonate water (100 mL) once and then with ethyl acetate (100 mL)/brine (80 mL) twice. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (N60: spherical neutral silica gel) with ethyl acetate/50% to 60% hexane containing 1% triethylamine to give 5′-O-(4,4′-dimethoxytrityl)-6-O-diphenylcarbamoyl-2-N-methylcarbamoyldeoxyguanosine (889 mg, 87%).

Workup

  1. customThen, the reaction was terminated
  2. additionby adding sodium bicarbonate water (5 mL)
  3. extractionThe reaction solution was extracted with ethyl acetate (100 mL)/sodium bicarbonate water (100 mL) once
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (N60: spherical neutral silica gel) with ethyl acetate/50% to 60% hexane containing 1% triethylamine

Sources & evidence

ORD record
ord-b0615bda978c494f959c54b7108bc02d
Source dataset
uspto-grants-2010_12
Patent number
US07851157B1

Reaction notes

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