Sodium Carbonate → HCID 67156804, compound

HRID 221608Notes

Reaction equation

HRID 221608 reaction equation
[C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C@@H:12]2[N:17]3[C:18]4[C:27]5[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=5)[N:21]=[CH:20][C:19]=4[N:28]=[C:16]3[CH2:15][O:14][CH2:13]2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].C1C=C(Cl)C=C(C(OO)=[O:37])C=1.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)(Cl)Cl>[C:1]([O:4][C:5]1[CH:6]=[CH:7][C:8]([CH2:11][C@@H:12]2[N:17]3[C:18]4[C:27]5[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=5)[N+:21]([O-:37])=[CH:20][C:19]=4[N:28]=[C:16]3[CH2:15][O:14][CH2:13]2)=[CH:9][CH:10]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 67156816HCID 67156816, compound

Product 1

HCID 67156804HCID 67156804, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

4-[(11S)-10,11-Dihydro-8H-[1,4]oxazino[4′,3′:1,2]imidazo[4,5-c]quinolin-11-ylmethyl]phenyl acetate (2.95 g, 7.91 mmol) was dissolved in 80 mL of CHCl3 and treated with MCPBA (2.33 g, 77% max). After stirring for 18 hours, the reaction was treated with 25 mL of a 2% Na2CO3 solution and the layers were separated. The aqueous layer was then extracted with CHCl3 (4×20 mL). The combined organic layers were washed with 20 mL of brine, dried over Na2SO4, filtered, and concentrated under reduced pressure to give 4-{[(11S)-5-oxido-10,11-dihydro-8H-[1,4]oxazino[4′,3′:1,2]imidazo[4,5-c]quinolin-11-yl]methyl}phenyl acetate (3.08 g) as a tan solid.

Workup

  1. customthe layers were separated
  2. extractionThe aqueous layer was then extracted with CHCl3 (4×20 mL)
  3. washThe combined organic layers were washed with 20 mL of brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-eb982700af9c4da5b3c21b19963563bd
Source dataset
uspto-grants-2012_06
Patent number
US08207162B2

Reaction notes

Loading…