m-Chloroperbenzoic acid → HCID 6483576, compound

HRID 856233Notes

Reaction equation

HRID 856233 reaction equation
[CH3:1][C@@:2]1([CH2:13][O:14][C:15]2[CH:20]=[CH:19][C:18]([N:21]3[CH2:26][CH2:25][S:24][CH2:23][CH2:22]3)=[CH:17][CH:16]=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:35])C=1>C(Cl)Cl>[CH3:1][C@@:2]1([CH2:13][O:14][C:15]2[CH:16]=[CH:17][C:18]([N:21]3[CH2:26][CH2:25][S:24](=[O:35])[CH2:23][CH2:22]3)=[CH:19][CH:20]=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 6483575HCID 6483575, compound

Product 1

HCID 6483576HCID 6483576, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(R)-2-Methyl-6-nitro-2-[4-(thiomorpholin-4-yl)phenoxymethyl]-2,3-dihydroimidazo[2,1-b]oxazole prepared in Example 137 (85 mg, 0.23 mmol) was dissolved in methylene chloride (5 ml). To the solution, m-chloroperbenzoic acid (59 mg, 0.24 mmol) was added followed by stirring at room temperature for 20 minutes. The reaction mixture was diluted with methylene chloride. The solution was washed with a sodium thiosulfate solution, a saturated sodium hydrogencarbonate solution and a saturated saline solution, dried over magnesium sulfate and then filtered. The resulting filtrate was concentrated under reduced pressure. The residue was crystallized from methylene chloride-isopropyl ether to afford (R)-2-methyl-6-nitro-2-[4-(1-oxothiomorpholin-4-yl)phenoxymethyl]-2,3-dihydroimidazo[2,1-b]oxazole (59 mg, yield 67%) as a white powder.

Workup

  1. washThe solution was washed with a sodium thiosulfate solution
  2. dry with materiala saturated sodium hydrogencarbonate solution and a saturated saline solution, dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationThe resulting filtrate was concentrated under reduced pressure
  5. customThe residue was crystallized from methylene chloride-isopropyl ether

Sources & evidence

ORD record
ord-912ac5deffc64f699d38ee3830fc1e9d
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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