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

HRID 1836222Notes

Reaction equation

HRID 1836222 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-daa90a20f55d4b47bf865bc8128b3873
Source dataset
uspto-grants-2004_08
Patent number
US06777395B2

Reaction notes

Loading…