m-Chloroperbenzoic acid → HCID 23081155, compound

HRID 856285Notes

Reaction equation

HRID 856285 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]([S:30][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.ClC1C=CC=C(C(OO)=[O:40])C=1>C(Cl)Cl>[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]([S:30]([CH3:31])=[O:40])=[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

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 23081294HCID 23081294, compound

Product 1

HCID 23081155HCID 23081155, compoundYield 65.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 4-methylsulfanylbenzyl 4-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl)piperazine-1-carboxylate prepared in Example 345 (300 mg, 0.67 mmol) and methylene chloride (10 ml), m-chloroperbenzoic acid (210 mg, 0.85 mmol) was added followed by stirring for 2 hours with cooling on ice-bath. The reaction mixture was washed with a saturated sodium sulfite solution, a saturated sodium hydrogencarbonate solution, and a saturated saline solution in this order, dried over sodium sulfate and then filtered. The filtrate was concentrated under reduced pressure, and the residue was recrystallized from isopropyl alcohol-ether to afford 4-methanesulfinylbenzyl 4-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl)piperazine-1-carboxylate (203 mg, yield 65%) as a white powder.

Workup

  1. additionwas added
  2. temperaturewith cooling on ice-bath
  3. washThe reaction mixture was washed with a saturated sodium sulfite solution
  4. dry with materiala saturated sodium hydrogencarbonate solution, and a saturated saline solution in this order, dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customthe residue was recrystallized from isopropyl alcohol-ether

Sources & evidence

ORD record
ord-cf2503749d69463091cde19f66f2eb2e
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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