1,1'-(Chlorophenylmethylene)bis(4-methoxybenzene) → HCID 13832357, compound

HRID 2260333Notes

Reaction equation

HRID 2260333 reaction equation
[S:1]([O:11][C@@H:12]1[C@H:16]([OH:17])[C@@H:15]([CH2:18][OH:19])[O:14][C@H:13]1[N:20]1[C:29]2[N:28]=[CH:27][N:26]=[C:24]([NH2:25])[C:23]=2[N:22]=[CH:21]1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].[CH3:30][O:31][C:32]1[CH:53]=[CH:52][C:35]([C:36](Cl)([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[C:37]2[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[CH:39][CH:38]=2)=[CH:34][CH:33]=1>N1C=CC=CC=1>[CH3:30][O:31][C:32]1[CH:53]=[CH:52][C:35]([C:36]([NH:25][C:24]2[C:23]3[N:22]=[CH:21][N:20]([C:29]=3[N:28]=[CH:27][N:26]=2)[C@@H:13]2[O:14][C@H:15]([CH2:18][O:19][C:36]([C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=3)([C:37]3[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[CH:39][CH:38]=3)[C:35]3[CH:34]=[CH:33][C:32]([O:31][CH3:30])=[CH:53][CH:52]=3)[C@@H:16]([OH:17])[C@H:12]2[O:11][S:1]([C:4]2[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=2)(=[O:2])=[O:3])([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[C:37]2[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[CH:39][CH:38]=2)=[CH:34][CH:33]=1

Participants

4

Reactant 2

HCID 968311,1'-(Chlorophenylmethylene)bis(4-methoxybenzene)HCID 10971862HCID 10971862, compound2×

Product 1

HCID 13832357HCID 13832357, compoundYield 75.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

2'-O-Tosyladenosine (Compound A1) (4.21 g, 10 mmol) and 4,4'-dimethoxytrityl chloride (7.45 g, 22 mmol) were added to anhydrous pyridine (50 ml), and stirred at room temperature for 20 hours. After ice cooling, 50% aqueous pyridine was added, the mixture was extracted with chloroform, and the organic layer was washed successively with aqueous sodium bicarbonate and water, and dried over magnesium sulfate. After distillating away the chloroform, the pyridine was removed by co-evaporation with toluene, and the residue was subjected to silica gel column chromatography eluant: toluene-ethyl acetate-triethylamine→(9:1:0.1) toluene-ethyl acetate-triethylamine-methanol (9:1:0.1:0.2)]. Fractions containing the desired substance were combined and concentrated to give Compound A2 (7.74 g, yield 75%).

Workup

  1. extractionthe mixture was extracted with chloroform
  2. washthe organic layer was washed successively with aqueous sodium bicarbonate and water
  3. dry with materialdried over magnesium sulfate
  4. customthe pyridine was removed by co-evaporation with toluene
  5. additionFractions containing the desired substance
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-0c62cfb2555547829ab054ee8c977a77
Source dataset
uspto-grants-1995_12
Patent number
US05476931

Reaction notes

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