Azidoethanol → 2-(4-((2-Nitro-1H-imidazol-1-yl)methyl)-1H-1,2,3-triazol-1-yl)ethanol

HRID 1011455노트

반응식

HRID 1011455 반응식
[N+:1]([C:4]1[N:5]([CH2:9][C:10]#[CH:11])[CH:6]=[CH:7][N:8]=1)([O-:3])=[O:2].[N:12]([CH:15](O)[CH3:16])=[N+:13]=[N-:14].[O:18]=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+]>[O-]S([O-])(=O)=O.[Cu+2].CO>[N+:1]([C:4]1[N:5]([CH2:9][C:10]2[N:14]=[N:13][N:12]([CH2:15][CH2:16][OH:18])[CH:11]=2)[CH:6]=[CH:7][N:8]=1)([O-:3])=[O:2]

참가 물질

6

반응물 3

HCID 22323701AzidoethanolHCID 23667548Sodium AscorbateHCID 546751432-Nitro-1-(prop-2-ynyl)-1H-imidazole

생성물 1

HCID 575402032-(4-((2-Nitro-1H-imidazol-1-yl)methyl)-1H-1,2,3-triazol-1-yl)ethanol수율 76.3%

시약·촉매·용매 2

HCID 24462Copper Sulfate촉매HCID 887Methanol용매

실험 절차

To a round bottom flask was added nitropropyne 10 (150 mg, 0.99 mmol) and azido ethanol (86 mg, 0.99 mmol). To this flask was added CuSO4 (0.04M, 100 uL) and sodium ascorbate (0.1 M, 100 uL). After 16 hrs, the reaction was poured onto EtOAc and washed with NH4OH. The organics were combined and the residue was purified on a combiflash system using EtOAc:Hex as the eluent followed by DCM:MeOH to afford 180 mg (76.3% yield) of 11 as a clear colorless oil. Mass Spec (lo-res): Calc'd for C8H14N6O3: 238.08; found: 239.10 (M+H).

후처리

  1. additionthe reaction was poured onto EtOAc
  2. washwashed with NH4OH
  3. customthe residue was purified on a combiflash system

출처 및 근거

ORD 기록
ord-69cea252800d4c5fb8a2b73772a18337
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07977361B2

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