1,1'-(Chlorophenylmethylene)bis(4-methoxybenzene) → HCID 131723176, compound

HRID 841089Notes

Reaction equation

HRID 841089 reaction equation
[C:1]([NH:9][C:10]1[C:11]2[N:12]=[CH:13][N:14]([C:32]=2[N:33]=[CH:34][N:35]=1)[C@@H:15]1[O:31][C@H:28]([CH2:29][OH:30])[C@@H:26]([OH:27])[C@H:16]1[O:17][C@@H:18]1[CH2:23][CH2:22][CH2:21][CH2:20][C@H:19]1[O:24][CH3:25])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.COC1C=CC([C:44](Cl)([C:51]2[CH:56]=[CH:55][C:54](OC)=[CH:53][CH:52]=2)[C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)=CC=1.[C:60](=[O:63])(O)[O-].[Na+]>N1C=CC=CC=1>[C:1]([NH:9][C:10]1[C:11]2[N:12]=[CH:13][N:14]([C:32]=2[N:33]=[CH:34][N:35]=1)[C@@H:15]1[O:31][C@H:28]([CH2:29][O:30][C:44]([C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[C:20]2[CH:21]=[CH:22][CH:23]=[C:18]([O:17][CH3:16])[C:19]=2[O:63][CH3:60])[C@@H:26]([OH:27])[C@H:16]1[O:17][C@@H:18]1[CH2:23][CH2:22][CH2:21][CH2:20][C@H:19]1[O:24][CH3:25])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 968311,1'-(Chlorophenylmethylene)bis(4-methoxybenzene)HCID 516892Sodium BicarbonateHCID 53790515HCID 53790515, compound

Product 1

HCID 131723176HCID 131723176, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Conditions

Temperature
25 °C

Procedure

A solution of N6-benzoyl-2′-O-(trans-2-methoxycyclohexyl)adenosine (0.285 mol) in pyridine (100 mL) is evaporated under reduced pressure to an oil. The residue is redissolved in dry pyridine (300 mL) and 4,4′-dimethoxytriphenylmethyl chloride (DMT-Cl, 10.9 g, 95%, 0.31 mol) added. The mixture is stirred at 25° C. for 16 h and then poured onto a solution of sodium bicarbonate (20 g) in ice water (500 mL). The product is extracted with ethyl acetate (2×150 mL). The organic layer is washed with brine (50 mL), dried over sodium sulfate (powdered) and evaporated under reduced pressure (below 40° C.). The residue is chromatographed on silica gel (400 g, ethyl acetate-hexane 1:1. Selected fractions were combined, concentrated under reduced pressure and dried at 25° C./0.2 mmHg to give the title compound.

Workup

  1. extractionThe product is extracted with ethyl acetate (2×150 mL)
  2. washThe organic layer is washed with brine (50 mL)
  3. dry with materialdried over sodium sulfate (powdered)
  4. customevaporated under reduced pressure (below 40° C.)
  5. customThe residue is chromatographed on silica gel (400 g, ethyl acetate-hexane 1:1
  6. concentrationconcentrated under reduced pressure
  7. customdried at 25° C./0.2 mmHg

Sources & evidence

ORD record
ord-94ddfb300a7c4ce7bbb77d0a3ec00adb
Source dataset
uspto-grants-2002_04
Patent number
US06369209B1

Reaction notes

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