1,1'-(Chlorophenylmethylene)bis(4-methoxybenzene) → HCID 86761228, compound

HRID 2262398Notes

Reaction equation

HRID 2262398 reaction equation
[C:1]([NH:4][C:5]1[N:6]=[C:7]([O:22][C:23](=[O:37])[N:24]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:8]2[N:9]=[CH:10][N:11]([C:20]=2[N:21]=1)[C@@H:12]1[O:19][C@H:16]([CH2:17][OH:18])[C@@H:14]([OH:15])[CH2:13]1)(=[O:3])[NH2:2].[CH3:38][O:39][C:40]1[CH:61]=[CH:60][C:43]([C:44](Cl)([C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=2)[C:45]2[CH:50]=[CH:49][C:48]([O:51][CH3:52])=[CH:47][CH:46]=2)=[CH:42][CH:41]=1.O.C(=O)(O)[O-].[Na+]>N1C=CC=CC=1>[C:1]([NH:4][C:5]1[N:6]=[C:7]([O:22][C:23](=[O:37])[N:24]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:8]2[N:9]=[CH:10][N:11]([C:20]=2[N:21]=1)[C@@H:12]1[O:19][C@H:16]([CH2:17][O:18][C:44]([C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=2)([C:45]2[CH:50]=[CH:49][C:48]([O:51][CH3:52])=[CH:47][CH:46]=2)[C:43]2[CH:42]=[CH:41][C:40]([O:39][CH3:38])=[CH:61][CH:60]=2)[C@@H:14]([OH:15])[CH2:13]1)(=[O:3])[NH2:2]

Participants

5

Reactant 3

HCID 968311,1'-(Chlorophenylmethylene)bis(4-methoxybenzene)HCID 86585896Sodium bicarbonate waterHCID 86761229HCID 86761229, compound

Product 1

HCID 86761228HCID 86761228, compoundYield 76.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

The above-obtained 2-N-carbamoyl-6-O-diphenylcarbamoyldeoxyguanosine (1.19 g, 2.35 mmol) was azeotroped with anhydrous pyridine three times and dissolved in anhydrous pyridine (23 mL), and 4,4′-dimethoxytrityl chloride (917 mg, 2.70 mmol) was added thereto. The mixture was stirred at room temperature for 2 hours, and sodium bicarbonate water (8 mL) was added thereto to terminate the reaction. Then, the reaction solution was extracted with ethyl acetate (150 mL)/sodium bicarbonate water (120 mL) once and then with ethyl acetate (150 mL)/brine (100 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 methanol/2% to 3% chloroform containing 1% triethylamine to give 2-N-carbamoyl-5′-O-(4,4′-dimethoxytrityl)-6-O-diphenylcarbamoyldeoxyguanosine (1.45 g, 76%).

Workup

  1. customto terminate
  2. customthe reaction
  3. extractionThen, the reaction solution was extracted with ethyl acetate (150 mL)/sodium bicarbonate water (120 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 methanol/2% to 3% chloroform containing 1% triethylamine

Sources & evidence

ORD record
ord-38700cc77094462a9db8482f5189b534
Source dataset
uspto-grants-2010_12
Patent number
US07851157B1

Reaction notes

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