Peracetic Acid → HCID 18783977, compound

HRID 1108649Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]1[C:25]2[C:24]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[N:18]=[CH:17][C:16]=2[N:15]=[C:14]1[CH3:26])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(OO)(=[O:29])C.C(=O)([O-])O.[Na+]>C(OCC)(=O)C.C(Cl)(Cl)Cl>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]1[C:25]2[C:24]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[N+:18]([O-:29])=[CH:17][C:16]=2[N:15]=[C:14]1[CH3:26])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 50 °C

Procedure

0.15 g (0.423 mmol) of 1-[4-(tert-butoxycarbonylamino)butyl]-2-methyl-1H-imidazo[4,5-c]quinoline) was dissolved in a mixed solvent of 5 ml of ethyl acetate and 5 ml of chloroform and 0.11 ml (0.508 mmol) of 32% peracetic acid was added thereto. The mixture was heated at 50° C. and stirred for 3 hours. After the reaction mixture was poured into a sodium hydrogencarbonate aqueous solution, the resulting solution was extracted with chloroform, dried (Na2SO4), then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:methanol=20:1 (v/v)) to obtain 0.13 g (0.351 mmol) of 1-[4-(tert-butoxycarbonylamino)butyl]-2-methyl-1H-imidazo[4,5-c]quinoline-5-oxide shown below as a white solid. ##STR59## Its spectroscopic data are as follows: IR (KBr) cm-1 : 3230, 2980, 1710, 1540, 1440, 1370, 1280, 1170, 880, 770.

Workup

additionwas added
extractionthe resulting solution was extracted with chloroform
dry with materialdried (Na2SO4)
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (chloroform:methanol=20:1 (v/v))

Sources & evidence

ORD record: ord-f25c430cbb294283ad91cb9ad40159a1
Source dataset: uspto-grants-2000_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06069149

Reaction notes

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