Sodium Carbonate → 2-[(11R)-5-oxido-10,11-dihydro-8H-[1,4]oxazino[4',3':1,2]imidazo[4,5-c]quinolin-11-yl]propan-2-ol

HRID 1035509Notes

Reaction equation

HRID 1035509 reaction equation
[CH:1]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:2]=1[C:3]1[N:13]3[C@@H:14]([C:18]([OH:21])([CH3:20])[CH3:19])[CH2:15][O:16][CH2:17][C:12]3=[N:11][C:4]=1[CH:5]=[N:6]2.C1C=C(Cl)C=C(C(OO)=[O:30])C=1.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[O-:30][N+:6]1[C:7]2[C:2](=[CH:1][CH:10]=[CH:9][CH:8]=2)[C:3]2[N:13]3[C@@H:14]([C:18]([OH:21])([CH3:19])[CH3:20])[CH2:15][O:16][CH2:17][C:12]3=[N:11][C:4]=2[CH:5]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 671569042-[(11R)-10,11-dihydro-8H-[1,4]oxazino[4',3':1,2]imidazo[4,5-c]quinolin-11-yl]propan-2-ol

Product 1

HCID 671565972-[(11R)-5-oxido-10,11-dihydro-8H-[1,4]oxazino[4',3':1,2]imidazo[4,5-c]quinolin-11-yl]propan-2-olYield 99.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-[(11R)-10,11-Dihydro-8H-[1,4]oxazino[4′,3′:1,2]imidazo[4,5-c]quinolin-11-yl]propan-2-ol (755 mg, 2.67 mmol) was dissolved in 30 mL of CH2Cl2 and treated with MCPBA (57-86%, 806 mg). After stirring for 75 minutes, the reaction was treated with 50 mL of 2% Na2CO3 solution and the layers were separated. The aqueous layer was then extracted with 10% methanol/CHCl3 (10×10 mL). The combined organic layers were washed with 10 mL of brine. The organic portion was then dried over Na2SO4, filtered and concentrated under reduced to give 2-[(11R)-5-oxido-10,11-dihydro-8H-[1,4]oxazino[4′,3′:1,2]imidazo[4,5-c]quinolin-11-yl]propan-2-ol (798 mg) as a light yellow solid.

Workup

  1. customthe layers were separated
  2. extractionThe aqueous layer was then extracted with 10% methanol/CHCl3 (10×10 mL)
  3. washThe combined organic layers were washed with 10 mL of brine
  4. dry with materialThe organic portion was then dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-16cb1ea57e584d469d1b9f91b0538140
Source dataset
uspto-grants-2013_10
Patent number
US08546383B2

Reaction notes

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