m-Chloroperbenzoic acid → HCID 54588459, compound

HRID 447273Notes

Reaction equation

HRID 447273 reaction equation
[N:1]1([C:6]2[N:11]=[CH:10][N:9]=[C:8]([NH:12][C:13]3[O:14][C@:15]4([CH2:23][N:24]=3)[CH:20]3[CH2:21][CH2:22][N:17]([CH2:18][CH2:19]3)[CH2:16]4)[CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.ClC1C=C(C=CC=1)C(OO)=[O:30]>C1COCC1>[N:1]1([C:6]2[N:11]=[CH:10][N:9]=[C:8]([NH:12][C:13]3[O:14][C@:15]4([CH2:23][N:24]=3)[CH:20]3[CH2:21][CH2:22][N+:17]([O-:30])([CH2:18][CH2:19]3)[CH2:16]4)[CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 59286554HCID 59286554, compound

Product 1

HCID 54588459HCID 54588459, compoundYield 95.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (R)—N-(6-(1H-imidazol-1-yl)pyrimidin-4-yl)-4H-1′-azaspiro[oxazole-5,3′-bicyclo[2.2.2]octan]-2-amine (52.9 mg, 0.163 mmol) and 3-chlorobenzoperoxoic acid (33.7 mg, 0.195 mmol) in 2 mL THF was stirred at room temperature for 24 h. The reaction was concentrated and the crude product was purified by flash chromatography on a 40 g silica gel cartridge with 20 to 40% [9:1 MeOH/NH4OH] in EtOAc, 40 min. Pure fractions were pooled, concentrated, and dried. The residue was dissolved in CDCl3, filtered through a 0.4μ filter, concentrated, and dried under high vacuum to yield (S)-2-(6-(1H-imidazol-1-yl)pyrimidin-4-ylamino)-4H-1′-azaspiro[oxazole-5,3′-bicyclo[2.2.2]octane]1′-oxide (53 mg, 95% yield).

Workup

  1. concentrationThe reaction was concentrated
  2. customthe crude product was purified by flash chromatography on a 40 g silica gel cartridge with 20 to 40% [9:1 MeOH/NH4OH] in EtOAc, 40 min
  3. concentrationconcentrated
  4. customdried
  5. dissolutionThe residue was dissolved in CDCl3
  6. filtrationfiltered through a 0.4μ filter
  7. concentrationconcentrated
  8. customdried under high vacuum

Sources & evidence

ORD record
ord-3f9e48e5f7b74b08a500b9a0930a1a4d
Source dataset
uspto-grants-2013_07
Patent number
US08481555B2

Reaction notes

Loading…