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

HRID 65659노트

반응식

HRID 65659 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-678d938fe117450c94947b855d5556e4
출처 데이터셋
uspto-grants-1978_12
특허 번호
US04128639

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