Tetrahydrofuran → HCID 59511056, compound

HRID 1157087Notes

Reaction equation

HRID 1157087 reaction equation
[N:1]([CH2:4][CH:5]([OH:8])[CH2:6][F:7])=[N+:2]=[N-:3].[C:9]([N:12]1[CH:16]=[CH:15][N:14]=[C:13]1[N+:17]([O-:19])=[O:18])#[C:10][CH3:11].C1COCC1.O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+]>[O-]S([O-])(=O)=O.[Cu+2].O.CC(O)(C)C>[F:7][CH2:6][CH:5]([OH:8])[CH2:4][N:1]1[CH:11]=[C:10]([CH2:9][N:12]2[CH:16]=[CH:15][N:14]=[C:13]2[N+:17]([O-:19])=[O:18])[N:3]=[N:2]1

Participants

8

Reactant 4

HCID 8028TetrahydrofuranHCID 23667548Sodium AscorbateHCID 59511048HCID 59511048, compoundHCID 66850847HCID 66850847, compound

Product 1

HCID 59511056HCID 59511056, compoundYield 4.2%

Reagents, catalysts & solvents 3

HCID 24462Copper SulfateCatalystHCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

To a vial was added fluoroazide 17 (690 mg, 5.79 mmol) and 1-propynyl-2-nitroimidazole (876 mg, 5.79 mmol). To this flask was added THF (3 mL), t-BuOH (3 mL), water (3 mL), CuSO4 (185 mg, 1.16 mmol) and sodium ascorbate (1.15 g, 5.79 mmol). After 16 hrs, the reaction was poured onto EtOAc and washed with NH4OH. The organics were combined and the material was then purified on a silica gel column using EtOAc:Hex as the eluent. The material was then further purified via recrystallization using EtOAc:Hex to afford 65 mg (4% yield) of pale yellow crystals. 1H NMR (DMSO-d6, 400 MHz), δ: 4.04 (1H, br d, J=20.4 Hz), 4.20-4.47 (4H, m), 5.53 (1H, br s), 5.66 (2H, s), 7.16, (1H, s), 7.68 (1H, s), 8.05 (1H, s).

Workup

  1. additionthe reaction was poured onto EtOAc
  2. washwashed with NH4OH
  3. customthe material was then purified on a silica gel column
  4. customThe material was then further purified via recrystallization

Sources & evidence

ORD record
ord-6db55d18b4a84144a98c14c9038648f7
Source dataset
uspto-grants-2010_10
Patent number
US07807394B2

Reaction notes

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