Methanol → N-[1-[(2R,4S,5R)-4-hydroxy-5-(trityloxymethyl)oxolan-2-yl]-2-oxopyrimidin-4-yl]benzamide

HRID 2393318Notes

Reaction equation

HRID 2393318 reaction equation
[C:1]([NH:9][C:10]1[CH:23]=[CH:22][N:13]([C@@H:14]2[O:21][C@H:18]([CH2:19][OH:20])[C@@H:16]([OH:17])[CH2:15]2)[C:12](=[O:24])[N:11]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[C:31](Cl)([C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.CO>C(Cl)Cl>[C:31]([O:20][CH2:19][C@H:18]1[O:21][C@@H:14]([N:13]2[CH:22]=[CH:23][C:10]([NH:9][C:1](=[O:8])[C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[N:11][C:12]2=[O:24])[CH2:15][C@@H:16]1[OH:17])([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)([C:44]1[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=1)[C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 1049PyridineHCID 6456Trityl chlorideHCID 9797617N4-Benzoyl-2'-deoxycytidine

Product 1

HCID 494349N-[1-[(2R,4S,5R)-4-hydroxy-5-(trityloxymethyl)oxolan-2-yl]-2-oxopyrimidin-4-yl]benzamideYield 26%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

3.31 g (10 mmol) of N-benzoyl-2'-deoxycytidine were added to 25 ml of pyridine, and then 3.07 g (11 mmol) of trityl chloride were added to the suspension. The resulting suspension was stirred at 100° C. for 1 hour, after which it was allowed to cool to room temperature. The pyridine was then removed by distillation under reduced pressure. The resulting residue was dissolved in a mixture of ethyl acetate and a saturated aqueous solution of sodium chloride. The organic layer was separated and washed twice, each time with a saturated aqueous solution of sodium chloride. The solution was then dried over anhydrous magnesium sulfate, after which the solvent was removed by distillation under reduced pressure. The resulting residue was purified by column chromatography through silica gel (Lober column Si-60, Size C) using a gradient elution method, with mixtures of methanol and methylene chloride ranging from 2:98 to 5:95 by volume as the eluent, to give 1.47 g (yield 26%) of the title compound.

Workup

  1. temperatureto cool to room temperature
  2. customThe pyridine was then removed by distillation under reduced pressure
  3. dissolutionThe resulting residue was dissolved in a mixture of ethyl acetate
  4. customThe organic layer was separated
  5. washwashed twice
  6. dry with materialThe solution was then dried over anhydrous magnesium sulfate
  7. customafter which the solvent was removed by distillation under reduced pressure
  8. customThe resulting residue was purified by column chromatography through silica gel (Lober column Si-60, Size C)
  9. washa gradient elution method

Sources & evidence

ORD record
ord-a06acc0e5ed04398ad8feaf705057117
Source dataset
uspto-grants-1998_09
Patent number
US05807837

Reaction notes

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