N,N-Diethylethanamine trihydrofluoride → 3'-Deoxy-3'-(iodomethyl)-2'-O-(2-methoxyethyl)-5-methyluridine

HRID 1270239ノート

反応式

HRID 1270239 の反応式
[Si]([O:18][CH2:19][C@H:20]1[O:24][C@@H:23]([N:25]2[CH:32]=[C:31]([CH3:33])[C:29](=[O:30])[NH:28][C:26]2=[O:27])[C@H:22]([O:34][CH2:35][CH2:36][O:37][CH3:38])[C@@H:21]1[CH2:39][I:40])(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.F.F.F.C(N(CC)CC)C>C1COCC1.C(OCC)(=O)C>[I:40][CH2:39][C@@H:21]1[C@@H:20]([CH2:19][OH:18])[O:24][C@@H:23]([N:25]2[CH:32]=[C:31]([CH3:33])[C:29](=[O:30])[NH:28][C:26]2=[O:27])[C@@H:22]1[O:34][CH2:35][CH2:36][O:37][CH3:38]

参加物

5

反応物 2

HCID 175505N,N-Diethylethanamine trihydrofluorideHCID 235183415'-O-(tert-butyldiphenylsilyl)-3'-deoxy-3'-(iodomethyl)-2'-O-(2-methoxyethyl)-5-methyluridine

生成物 1

HCID 235183313'-Deoxy-3'-(iodomethyl)-2'-O-(2-methoxyethyl)-5-methyluridine収率 69.4%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of 5′-O-(tert-butyldiphenylsilyl)-3′-deoxy-3′-(iodomethyl)-2′-O-(2-methoxyethyl)-5-methyluridine (1.12 g, 1.65 mmol) and triethylamine trihydrofluoride (1.1 mL, 1.1 g, 6.7 mmol) in 20 mL of THF was stirred at rt for 24 h. The reaction mixture was diluted with 50 mL of ethyl acetate and washed with water and brine. The organic phase was dried (Na2SO4) and concentrated. The residue was purified by flash chromatography on a silica gel column. Gradient elution with 2:1, 1:2 and then 1:3 hexanes-EtOAc provided 504 mg of the title compound as a white foam.

後処理

  1. washwashed with water and brine
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. concentrationconcentrated
  4. customThe residue was purified by flash chromatography on a silica gel column
  5. washGradient elution with 2:1, 1:2

出典と根拠

ORDレコード
ord-e2db42fe3984474fb43787c3ebc60974
出典データセット
uspto-grants-2007_04
特許番号
US07202224B2

反応ノート

読み込み中…