Sodium Nitrite → 5'-(3-Methyl-3-nitrosoureido)-5'-deoxythymidine

HRID 65659ノート

反応式

HRID 65659 の反応式
[CH3:1][NH:2][C:3](=[O:21])[NH:4][CH2:5][C@H:6]1[O:10][C@@H:9]([N:11]2[CH:19]=[C:17]([CH3:18])[C:15](=[O:16])[NH:14][C:12]2=[O:13])[CH2:8][C@@H:7]1[OH:20].[N:22]([O-])=[O:23].[Na+]>C(O)(=O)C>[CH3:1][N:2]([N:22]=[O:23])[C:3](=[O:21])[NH:4][CH2:5][C@H:6]1[O:10][C@@H:9]([N:11]2[CH:19]=[C:17]([CH3:18])[C:15](=[O:16])[NH:14][C:12]2=[O:13])[CH2:8][C@@H:7]1[OH:20]

参加物

4

反応物 2

HCID 23668193Sodium NitriteHCID 540012745'-(3-Methylureido)-5'-deoxythymidine

生成物 1

HCID 541182865'-(3-Methyl-3-nitrosoureido)-5'-deoxythymidine収率 70.2%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

To a solution of 4 (1.00 g, 3.35 mmol) in 50% aqueous acetic acid at 0°, sodium nitrite (0.31 g, 4.55 mmol) was added slowly. The reaction mixture was kept at 0° with stirring for 3 h, during which time crystals started to precipitate out. The product was collected by filtration, washed with water, cooled methanol, ether, and dried. The filtrate was concentrated and an additional fraction of crystals was obtained. The combined product was recrystallized from methanol to yield 0.77 g (70%) of white fine needles: mp 159°-160° dec.: uvλmaxEtOH 264 nm (ε11,000); uvλminEtOH 235 nm. Anal. (C12H17N5O6) C, H, N.

後処理

  1. customwas kept at 0°
  2. customto precipitate out
  3. filtrationThe product was collected by filtration
  4. washwashed with water
  5. temperaturecooled methanol, ether
  6. customdried
  7. concentrationThe filtrate was concentrated
  8. customan additional fraction of crystals was obtained
  9. customThe combined product was recrystallized from methanol

出典と根拠

ORDレコード
ord-678d938fe117450c94947b855d5556e4
出典データセット
uspto-grants-1978_12
特許番号
US04128639

反応ノート

読み込み中…