Tetrahydrofuran → HCID 23081386, compound

HRID 856286Notes

Reaction equation

HRID 856286 reaction equation
[CH3:1][C:2]1([CH2:13][N:14]2[CH2:19][CH2:18][N:17]([C:20]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][C:27]([O:30][Si](C(C)(C)C)(C)C)=[CH:26][CH:25]=3)=[O:21])[CH2:16][CH2:15]2)[O:6][C:5]2=[N:7][C:8]([N+:10]([O-:12])=[O:11])=[CH:9][N:4]2[CH2:3]1.C1COCC1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C(OCC)(=O)C>[CH3:1][C:2]1([CH2:13][N:14]2[CH2:15][CH2:16][N:17]([C:20]([O:22][CH2:23][C:24]3[CH:25]=[CH:26][C:27]([OH:30])=[CH:28][CH:29]=3)=[O:21])[CH2:18][CH2:19]2)[O:6][C:5]2=[N:7][C:8]([N+:10]([O-:12])=[O:11])=[CH:9][N:4]2[CH2:3]1

Participants

5

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 2724141Tetrabutylammonium FluorideHCID 23081300HCID 23081300, compound

Product 1

HCID 23081386HCID 23081386, compoundYield 30.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 4-(tert-butyldimethylsilanyloxy)benzyl 4-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl)piperazine-1-carboxylate (400 mg, 0.75 mmol) and THF(10 ml), a 1M solution of tetrabutylammonium fluoride in THF (0.8 ml, 0.8 mmol) was added followed by stirring for 20 minutes with cooling on ice-bath. To the reaction mixture, ethyl acetate was added, and the solution was washed with a saturated ammonium chloride solution, water and a saturated saline solution in this order, dried over magnesium sulfate and then filtered. The filtrate was concentrated under reduced pressure. To the residue, diethyl ether was added, and the precipitates were filtered off to afford 4-hydroxybenzyl 4-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl)piperazine-1-carboxylate (95 mg, yield 30%) as a light yellow powder.

Workup

  1. temperaturewith cooling on ice-bath
  2. washthe solution was washed with a saturated ammonium chloride solution, water
  3. dry with materiala saturated saline solution in this order, dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. additionTo the residue, diethyl ether was added
  7. filtrationthe precipitates were filtered off

Sources & evidence

ORD record
ord-da82e900ed8b4f55a6dab12c6402b249
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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