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

HRID 1245504ノート

反応式

HRID 1245504 の反応式
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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-0b5c01a30b62480eb1dcf0dc11d2fd2e
出典データセット
uspto-grants-2006_10
特許番号
US07125855B2

反応ノート

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