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

HRID 1358696ノート

反応式

HRID 1358696 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 20230201dichloroethane DMSO溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-68c5885cd720466eba66ef062d0fd6aa
出典データセット
uspto-grants-2003_07
特許番号
US06596858B2

反応ノート

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