Tetrahydrofuran → HCID 59511056, compound

HRID 1011462Notes

Reaction equation

HRID 1011462 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-20cadc0915144f008c276cf6fe01c61a
Source dataset
uspto-grants-2011_07
Patent number
US07977361B2

Reaction notes

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