1,1'-(Chlorophenylmethylene)bis(4-methoxybenzene) → HCID 136381141, compound

HRID 54638Notes

Reaction equation

HRID 54638 reaction equation
[N:1]#[N:2].[C:3]1([CH2:9][C:10]([C@@:12]2([N:20]3[C:30]4[N:29]=[C:27]([NH2:28])[NH:26][C:24](=[O:25])[C:23]=4[N:22]=[CH:21]3)[O:19][C@H:16]([CH2:17][OH:18])[C@@H:14]([OH:15])[CH2:13]2)=[O:11])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:31][O:32][C:33]1[CH:54]=[CH:53][C:36]([C:37](Cl)([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[C:38]2[CH:43]=[CH:42][C:41]([O:44][CH3:45])=[CH:40][CH:39]=2)=[CH:35][CH:34]=1>N1C=CC=CC=1>[N:1]#[N:2].[C:3]1([CH2:9][C:10]([C@@:12]2([N:20]3[C:30]4[N:29]=[C:27]([NH2:28])[NH:26][C:24](=[O:25])[C:23]=4[N:22]=[CH:21]3)[O:19][C@H:16]([CH2:17][O:18][C:37]([C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)([C:38]3[CH:43]=[CH:42][C:41]([O:44][CH3:45])=[CH:40][CH:39]=3)[C:36]3[CH:35]=[CH:34][C:33]([O:32][CH3:31])=[CH:54][CH:53]=3)[C@@H:14]([OH:15])[CH2:13]2)=[O:11])[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 968311,1'-(Chlorophenylmethylene)bis(4-methoxybenzene)HCID 136381139N2 (phenylacetyl)-2'-deoxyguanosine

Product 1

HCID 136381141HCID 136381141, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Conditions

Temperature
5 °C

Procedure

N2 -(Phenylacetyl)-2'-deoxyguanosine (2a) (23.12 g, 60 mmoles) was dried by coevaporation with dry pyridine (2×100 ml), dissolved in 600 ml of dry pyridine and ice cooled. To this solution, 4,4'-dimethoxytrityl chloride (25.5 g, 72 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 600 ml of methylene chloride, washed successively with 2×400 ml of 5% NaHCO3 and 1×400 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 (6×50 cm) by gradient elution with 1L 0-6% methylene chloride-methanol. The desired fractions were collected, concentrated to about 100 ml and added dropwise to 1.5L cooled hexane (0° C.) to precipitate the product. The precipitated product was filtered, washed with hexane and air dried to yield 24 g (58%) of tritylated product (3a), as confirmed by spectroscopic and elemental analysis.

Workup

  1. temperatureice cooled
  2. customAfter removing the pyridine under reduced pressure
  3. washwashed successively with 2×400 ml of 5% NaHCO3 and 1×400 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 (6×50 cm) by gradient elution with 1L 0-6% methylene chloride-methanol
  7. customThe desired fractions were collected
  8. concentrationconcentrated to about 100 ml
  9. additionadded dropwise to 1.5L
  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-c10f926adc434de584c260ccd5a163fa
Source dataset
uspto-grants-1997_04
Patent number
US05623068

Reaction notes

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