1,1'-(Chlorophenylmethylene)bis(4-methoxybenzene) → 5'-O-(4,4'-Dimethoxytrityl)-2'-O-[2-(N-methylcarbamoyl)ethyl]uridine

HRID 1665822Notes

Reaction equation

HRID 1665822 reaction equation
[CH3:1][NH:2][C:3]([CH2:5][CH2:6][O:7][C@@H:8]1[C@H:12]([OH:13])[C@@H:11]([CH2:14][OH:15])[O:10][C@H:9]1[N:16]1[CH:23]=[CH:22][C:20](=[O:21])[NH:19][C:17]1=[O:18])=[O:4].[CH3:24][O:25][C:26]1[CH:47]=[CH:46][C:29]([C:30](Cl)([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[C:31]2[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=2)=[CH:28][CH:27]=1>N1C=CC=CC=1>[CH3:38][O:37][C:34]1[CH:33]=[CH:32][C:31]([C:30]([O:15][CH2:14][C@H:11]2[O:10][C@@H:9]([N:16]3[CH:23]=[CH:22][C:20](=[O:21])[NH:19][C:17]3=[O:18])[C@H:8]([O:7][CH2:6][CH2:5][C:3](=[O:4])[NH:2][CH3:1])[C@@H:12]2[OH:13])([C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)[C:29]2[CH:46]=[CH:47][C:26]([O:25][CH3:24])=[CH:27][CH:28]=2)=[CH:36][CH:35]=1

Participants

4

Reactant 2

HCID 968311,1'-(Chlorophenylmethylene)bis(4-methoxybenzene)HCID 532538162'-O-[2-(N-Methylcarbamoyl)ethyl]uridine

Product 1

HCID 532538595'-O-(4,4'-Dimethoxytrityl)-2'-O-[2-(N-methylcarbamoyl)ethyl]uridineYield 71%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The compound (558 mg, 1.67 mmol) prepared in Example 6 was dissolved in dried pyridine (8 mL). To the solution was added 4,4′-dimethoxytrityl chloride (622 mg, 1.84 mmol), followed by stirring at room temperature. The reaction system was concentrated under reduced pressure, diluted with ethyl acetate, and then washed with a saturated sodium hydrogen carbonate aqueous solution. The organic layer was dried with anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography eluting with chloroform:methanol (98:2, v/v) containing 0.5% triethylamine to give the title compound (749 mg, 70%).

Workup

  1. concentrationThe reaction system was concentrated under reduced pressure
  2. additiondiluted with ethyl acetate
  3. washwashed with a saturated sodium hydrogen carbonate aqueous solution
  4. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. washeluting with chloroform:methanol (98:2
  8. additionv/v) containing 0.5% triethylamine

Sources & evidence

ORD record
ord-2c3c5caa19784d44aa3bb5e4a746afcc
Source dataset
uspto-grants-2011_10
Patent number
US08039611B2

Reaction notes

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