1,1'-(Chlorophenylmethylene)bis(4-methoxybenzene) → HCID 136381145, compound

HRID 54640Notes

Reaction equation

HRID 54640 reaction equation
[N:1]#[N:2].[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH2:11][C:12]([C@@:14]2([N:22]3[C:32]4[N:31]=[C:29]([NH2:30])[NH:28][C:26](=[O:27])[C:25]=4[N:24]=[CH:23]3)[O:21][C@H:18]([CH2:19][OH:20])[C@@H:16]([OH:17])[CH2:15]2)=[O:13])[CH:8]=[CH:9][CH:10]=1.[CH3:33][O:34][C:35]1[CH:56]=[CH:55][C:38]([C:39](Cl)([C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[C:40]2[CH:45]=[CH:44][C:43]([O:46][CH3:47])=[CH:42][CH:41]=2)=[CH:37][CH:36]=1>N1C=CC=CC=1>[N:1]#[N:2].[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH2:11][C:12]([C@@:14]2([N:22]3[C:32]4[N:31]=[C:29]([NH2:30])[NH:28][C:26](=[O:27])[C:25]=4[N:24]=[CH:23]3)[O:21][C@H:18]([CH2:19][O:20][C:39]([C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)([C:40]3[CH:45]=[CH:44][C:43]([O:46][CH3:47])=[CH:42][CH:41]=3)[C:38]3[CH:37]=[CH:36][C:35]([O:34][CH3:33])=[CH:56][CH:55]=3)[C@@H:16]([OH:17])[CH2:15]2)=[O:13])[CH:8]=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 968311,1'-(Chlorophenylmethylene)bis(4-methoxybenzene)HCID 136381143N2 (3-methoxyphenylacetyl)-2'-deoxyguanosine

Product 1

HCID 136381145HCID 136381145, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Conditions

Temperature
5 °C

Procedure

N2 -(3-Methoxyphenylacetyl)-2'-deoxyguanosine (2b) (2.08 g, 5 mmoles) was dried by coevaporation with dry pyridine (2×30 ml), dissolved in 40 ml of dry pyridine and ice cooled. To this solution, 4,4'-dimethoxytrityl chloride (2.2 g, 6.5 mmoles) was added. The reaction mixture was stirred at 5° C. for 20 hours. After removing the pyridine under reduced pressure, the resulting residue was taken up in 150 ml of methylene chloride and washed successively with 2×100 ml of 5% NaHCO3 and 1×100 ml of water. The organic layer was dried over anhydrous sodium sulfate and concentrated to near dryness. The product was purified on a silica gel column (2×40 cm) by gradient elution with 200 ml 0-6% methylene chloride-methanol. The desired fractions were collected, concentrated to about 30 ml and added dropwise to 200 ml cooled hexane (0° C.) to precipitate the product. The precipitated product was filtered, washed with hexane and air dried to yield 1.7 g (47%) of tritylated product (3b), as confirmed by spectroscopic and elemental analysis.

Workup

  1. temperatureice cooled
  2. customAfter removing the pyridine under reduced pressure
  3. washwashed successively with 2×100 ml of 5% NaHCO3 and 1×100 ml of water
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe product was purified on a silica gel column (2×40 cm) by gradient elution with 200 ml 0-6% methylene chloride-methanol
  7. customThe desired fractions were collected
  8. concentrationconcentrated to about 30 ml
  9. additionadded dropwise to 200 ml
  10. temperaturecooled hexane (0° C.)
  11. customto precipitate the product
  12. filtrationThe precipitated product was filtered
  13. washwashed with hexane and air
  14. customdried

Sources & evidence

ORD record
ord-9c2d06a7275141b5a5e3a8630e9810a5
Source dataset
uspto-grants-1997_04
Patent number
US05623068

Reaction notes

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