Tert-Butyl nitrite → Adenosine,2-bromo-2'-deoxy-(9CI)

HRID 1358696

반응식

HRID 1358696 반응식
[CH:1]1[N:9]([C@@H:10]2[O:14][C@H:13]([CH2:15][OH:16])O[CH2:11]2)[C:8]2[N:7]=[C:6](N)[N:5]=[C:4]([NH2:18])[C:3]=2[N:2]=1.[Sb](Br)(Br)[Br:20].N([O:25][C:26](C)(C)C)=O.C(#N)C.O>ClC(Cl)C.CS(C)=O.C(O)(=O)C>[Br:20][C:6]1[N:5]=[C:4]([NH2:18])[C:3]2[N:2]=[CH:1][N:9]([C:8]=2[N:7]=1)[C@@H:10]1[O:14][C@H:13]([CH2:15][OH:16])[C@@H:26]([OH:25])[CH2:11]1

참가 물질

7

반응물 4

HCID 10906Tert-Butyl nitriteHCID 24615Antimony tribromideHCID 124088AmdoxovirHCID 18373917Acetonitrile--water (1/1)

생성물 1

HCID 10065192Adenosine,2-bromo-2'-deoxy-(9CI)

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 20230201dichloroethane DMSO용매

반응 조건

온도
0 °C

실험 절차

DAPD (2 g, 7.5 mmol) was suspended in 170 mL dichloroethane/DMSO (4:1) and cooled to 0° C. under an inert atmosphere. To this was added antimony tribromide (3.8 g, 10.5 mmol) and tert-butyl nitrite (1.85 mL, 1.6 g, 15.5 mmol) followed by stirring while allowing the reaction to warm to room temperature. Analysis by HPLC [Novapak C-18; 5% acetonitrile/water, 0.1M TEA, pH 7 with acetic acid] revealed a new peak that eluted at 5.59 minutes (a retention time that was expected for the brominated product) with concomitant loss of DAPD starting material. The reaction was stirred overnight and quenched with triethylamine. The conversion by HPLC was 26% indicating the synthesis of 2-bromo-2′-deoxyadenosine.

후처리

  1. customthe reaction
  2. temperatureto warm to room temperature
  3. washthat eluted at 5.59 minutes (a retention time that
  4. stirringThe reaction was stirred overnight
  5. customquenched with triethylamine
  6. customthe synthesis of 2-bromo-2′-deoxyadenosine

출처 및 근거

ORD 기록
ord-68c5885cd720466eba66ef062d0fd6aa
출처 데이터셋
uspto-grants-2003_07
특허 번호
US06596858B2

연결된 노트

불러오는 중…