Hydrochloric Acid → HCID 23081597, compound

HRID 856287Notes

Reaction equation

HRID 856287 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]([C:30](OC)([O:32]C)[CH3:31])=[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.Cl.C(=O)([O-])O.[Na+]>C1COCC1>[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]([C:30](=[O:32])[CH3:31])=[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 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 23081520HCID 23081520, compound

Product 1

HCID 23081597HCID 23081597, compoundYield 102.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-(1,1-dimethoxyethyl)benzyl 4-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl)piperazine-1-carboxylate (600 mg, 1.23 mmol), 1 N hydrochloric acid (10 ml, 10 mmol) and THF (15 ml) was stirred at room temperature for 2 hours, then neutralized with a saturated sodium hydrogencarbonate solution, and the resulting mixture was extracted with ethyl acetate. The oranic phase was washed with water and then with a saturated saline solution, 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-acetylbenzyl 4-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl)piperazine-1-carboxylate (558 mg, yield 99%) as a white powder.

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate
  2. washThe oranic phase was washed with water
  3. dry with materialwith a saturated saline solution, 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-76f66804ceed430d8b72447516e480c5
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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