Water → HCID 58527476, compound

HRID 1803401Notes

Reaction equation

HRID 1803401 reaction equation
[CH3:1][S:2][CH2:3][C@@H:4]1[N:9]2[C:10]3[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[N:13]=[C:12]([NH2:20])[C:11]=3[N:21]=[C:8]2[CH2:7][O:6][CH2:5]1.C1C=C(Cl)C=C(C(OO)=[O:30])C=1.C([O-])([O-])=O.[Na+].[Na+].[OH2:39]>C(Cl)(Cl)Cl>[CH3:1][S:2]([CH2:3][C@@H:4]1[N:9]2[C:10]3[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[N:13]=[C:12]([NH2:20])[C:11]=3[N:21]=[C:8]2[CH2:7][O:6][CH2:5]1)(=[O:30])=[O:39]

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 58527466HCID 58527466, compound

Product 1

HCID 58527476HCID 58527476, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of (11R)-11-[(methylthio)methyl]-10,11-dihydro-8H-[1,4]oxazino[4′,3′:1,2]imidazo[4,5-c]quinolin-6-amine (640 mg, 2.1 mmol) dissolved in 10 mL of CHCl3 was cooled to 0° C. and treated with MCPBA (50% purity, 1.2 g, 4.3 mmol). The reaction mixture was warmed to ambient temperature over 1 hour. The resulting light brown reaction mixture was treated with 2 N aqueous Na2CO3 solution, diluted with water, and extracted with CHCl3. The organic layer was dried over Na2SO4, filtered and then concentrated under reduced pressure to give a brown oil. Chromatography (SiO2, 0-30% CMA/CHCl3) gave the desired product as an oil. The oil was slurried in acetonitrile to produce a solid which was isolated by filtration to give 250 mg of the title compound as a white solid, mp 158-161° C.

Workup

  1. temperatureThe reaction mixture was warmed to ambient temperature over 1 hour
  2. extractionextracted with CHCl3
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto give a brown oil

Sources & evidence

ORD record
ord-34fa267e3841444fa3d1192dc1329a2d
Source dataset
uspto-grants-2013_01
Patent number
US08350034B2

Reaction notes

Loading…