Acetic Acid → HCID 68973958, compound

HRID 540928Notes

Reaction equation

HRID 540928 reaction equation
[CH2:1]([C:3]1[N:4]([CH2:27][CH:28]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29]2)[C:5]2[C:14]3[CH:13]=[CH:12][C:11]([O:15][CH2:16][CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:10][C:9]=3[N:8]=[CH:7][C:6]=2[N:26]=1)[CH3:2].C(OO)(=[O:36])C.C(O)(=O)C.S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>C(OCC)(=O)C.O>[CH2:1]([C:3]1[N:4]([CH2:27][CH:28]2[CH2:29][CH2:30][O:31][CH2:32][CH2:33]2)[C:5]2[C:14]3[CH:13]=[CH:12][C:11]([O:15][CH2:16][CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:22])[CH3:23])=[CH:10][C:9]=3[N+:8]([O-:36])=[CH:7][C:6]=2[N:26]=1)[CH3:2]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 6585Peracetic Acid2×HCID 656671Sodium PyrosulfiteHCID 69506987HCID 69506987, compound

Product 1

HCID 68973958HCID 68973958, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

tert-Butyl 2-{[2-ethyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-imidazo[4,5-c]quinolin-7-yl]oxy}ethylcarbamate (2.3 g, 5.06 mmol) was slurried in ethyl acetate (20 mL). 32% Peracetic acid in acetic acid (1.06 mL, 5.06 mmol) was added in one portion and the reaction was heated to 50° C. for 2 hours. Another 0.250 mL (1.19 mmol) peracetic acid solution was added and the reaction was stirred for 1 additional hour. Sodium metabisulfite (1.2 g, 6.33 mmol) in water (2.5 mL) was added over 3 minutes and the reaction was stirred for 30 minutes. The heat was removed and the reaction was brought to pH 10 with saturated aqueous sodium carbonate (˜10 mL). The milky slurry was cooled in an ice bath and subsequently filtered. The solid was washed with water and dried for 1 hour. Roughly 2.0 g of tert-butyl 2-{[2-ethyl-5-oxido-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-imidazo[4,5-c]quinolin-7-yl]oxy}ethylcarbamate was isolated as an off-white solid with water still remaining.

Workup

  1. stirringthe reaction was stirred for 30 minutes
  2. customThe heat was removed
  3. temperatureThe milky slurry was cooled in an ice bath
  4. filtrationsubsequently filtered
  5. washThe solid was washed with water
  6. customdried for 1 hour

Sources & evidence

ORD record
ord-45d648fbe02b41eb85ca178a51024459
Source dataset
uspto-grants-2014_10
Patent number
US08871782B2

Reaction notes

Loading…