Trifluoroacetic acid → 3'-Deoxy-2'-o-(2-methoxyethyl)-3'-methyl-5-methyluridine

HRID 2212900Notes

Reaction equation

HRID 2212900 reaction equation
FC(F)(F)C(O)=O.COC1C=CC(C([O:27][CH2:28][C@H:29]2[O:33][C@@H:32]([N:34]3[CH:41]=[C:40]([CH3:42])[C:38](=[O:39])[NH:37][C:35]3=[O:36])[C@H:31]([O:43][CH2:44][CH2:45][O:46][CH3:47])[C@@H:30]2[CH3:48])(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C(Cl)(Cl)Cl>[CH3:48][C@@H:30]1[C@@H:29]([CH2:28][OH:27])[O:33][C@@H:32]([N:34]2[CH:41]=[C:40]([CH3:42])[C:38](=[O:39])[NH:37][C:35]2=[O:36])[C@@H:31]1[O:43][CH2:44][CH2:45][O:46][CH3:47]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 235183333'-Deoxy-5'-O-(4-methoxytrityl)-3'-methyl-2'-O-(2-methoxyethyl)-5-methyluridine

Product 1

HCID 99228483'-Deoxy-2'-o-(2-methoxyethyl)-3'-methyl-5-methyluridineYield 85.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Trifluoroacetic acid (1.5 mL) was added dropwise to a stirred solution of 3′-deoxy-5′-O-(4-methoxytrityl)-3′-methyl-2′-O-(2-methoxyethyl)-5-methyluridine (370 mg, 0.63 mmol) in 50 mL of chloroform at 0° C. The mixture was stirred at rt for 30 min, concentrated, and then dissolved in ethyl acetate. The solution was washed with dilute sodium bicarbonate and brine. The organic phase was dried (Na2SO4) and concentrated. The resulting residue was purified by flash chromatography on a silica gel column. Elution with 1:1, 1:3 and then 0:1 hexanes-EtOAc provided 170 mg of the title compound as a white foam.

Workup

  1. concentrationconcentrated
  2. dissolutiondissolved in ethyl acetate
  3. washThe solution was washed with dilute sodium bicarbonate and brine
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. concentrationconcentrated
  6. customThe resulting residue was purified by flash chromatography on a silica gel column
  7. washElution with 1:1, 1:3

Sources & evidence

ORD record
ord-9d24e54aaf7f4f0597827d85598d6d48
Source dataset
uspto-grants-2006_09
Patent number
US07105499B2

Reaction notes

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