1,1'-(Chlorophenylmethylene)bis(4-methoxybenzene) → HCID 54360919, compound

HRID 481018Notes

Reaction equation

HRID 481018 reaction equation
[C:1]([NH:9][C:10]1[C:11]2[N:12]=[CH:13][N:14]([C:28]=2[N:29]=[CH:30][N:31]=1)[C@@H:15]1[O:27][C@H:24]([CH2:25][OH:26])[C@@H:18]([O:19][CH2:20][CH2:21][O:22][CH3:23])[C@H:16]1[OH:17])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:32][O:33][C:34]1[CH:55]=[CH:54][C:37]([C:38](Cl)([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[C:39]2[CH:44]=[CH:43][C:42]([O:45][CH3:46])=[CH:41][CH:40]=2)=[CH:36][CH:35]=1.C(=O)(O)[O-].[Na+]>N1C=CC=CC=1>[C:1]([NH:9][C:10]1[C:11]2[N:12]=[CH:13][N:14]([C:28]=2[N:29]=[CH:30][N:31]=1)[C@@H:15]1[O:27][C@H:24]([CH2:25][O:26][C:38]([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)([C:39]2[CH:44]=[CH:43][C:42]([O:45][CH3:46])=[CH:41][CH:40]=2)[C:37]2[CH:36]=[CH:35][C:34]([O:33][CH3:32])=[CH:55][CH:54]=2)[C@@H:18]([O:19][CH2:20][CH2:21][O:22][CH3:23])[C@H:16]1[OH:17])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 968311,1'-(Chlorophenylmethylene)bis(4-methoxybenzene)HCID 516892Sodium BicarbonateHCID 54479467HCID 54479467, compound

Product 1

HCID 54360919HCID 54360919, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Conditions

Temperature
25 °C

Procedure

A solution of N6-Benzoyl-3′-O-(2-methoxyethyl) adenosine (11.0 g, 0.285 mol) in pyridine (100 mL) was evaporated under reduced pressure to an oil. The residue was redissolved in dry pyridine (300 mL) and 4,4′-dimethoxytrityl chloride (DMT-Cl, 10.9 g, 95%, 0.31 mol) was added. The mixture was 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 was extracted with ethyl acetate (2×150 mL). The organic layer was washed with brine (50 mL), dried over sodium sulfate (powdered) and evaporated under reduced pressure (below 40° C.). The residue was chromatographed on silica gel (400 g, ethyl acetate-acetonitrile-triethylamine 99:1:1→95:5:1). Selected fractions were combined, concentrated under reduced pressure and dried at 25° C./0.2 mmHg to give 16.8 g (73%) of foam; TLC homogenous.

Workup

  1. extractionThe product was extracted with ethyl acetate (2×150 mL)
  2. washThe organic layer was washed with brine (50 mL)
  3. dry with materialdried over sodium sulfate (powdered)
  4. customevaporated under reduced pressure (below 40° C.)
  5. customThe residue was chromatographed on silica gel (400 g, ethyl acetate-acetonitrile-triethylamine 99:1:1→95:5:1)
  6. concentrationconcentrated under reduced pressure
  7. customdried at 25° C./0.2 mmHg

Sources & evidence

ORD record
ord-c7de2dfd3b714e1698353201a494ddd8
Source dataset
uspto-grants-2003_11
Patent number
US06653458B1

Reaction notes

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