m-Chloroperbenzoic acid → HCID 25126882, compound

HRID 1672754Notes

Reaction equation

HRID 1672754 reaction equation
[C:1]([C:3]1[CH:26]=[CH:25][C:6]([CH2:7][N:8]2[CH2:17][C@H:16]3[N:12]([CH2:13][CH2:14][CH2:15]3)[C:11]3[N:18]=[C:19](SC)[N:20]=[CH:21][C:10]=3[C:9]2=[O:24])=[CH:5][CH:4]=1)#[N:2].ClC1C=CC=C(C(OO)=O)C=1.C(=O)(O)[O-].[Na+].[CH2:43]([NH2:45])[CH3:44].C1COCC1>ClCCl>[C:1]([C:3]1[CH:26]=[CH:25][C:6]([CH2:7][N:8]2[CH2:17][C@H:16]3[N:12]([CH2:13][CH2:14][CH2:15]3)[C:11]3[N:18]=[C:19]([NH:45][CH2:43][CH3:44])[N:20]=[CH:21][C:10]=3[C:9]2=[O:24])=[CH:5][CH:4]=1)#[N:2]

Participants

6

Reactant 4

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 66726184Ethylamine tetrahydrofuranHCID 67351119HCID 67351119, compound

Product 1

HCID 25126882HCID 25126882, compoundYield 67.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-5-(4-Cyanobenzyl)-9-methylthio-1,2,3,3a,4,5-hexahydro-5,8,10,10b-tetraazabenzo[e]azulen-6-one (0.927 g, 2.54 mmol) obtained in Step 2 was dissolved in dichloromethane (10 mL), and the mixture was stirred at room temperature for 30 minutes after adding 3-chloroperbenzoic acid (65%; 1.01 g, 3.81 mmol). Thereafter, an aqueous sodium bicarbonate solution was added to the reaction mixture, and the mixture was extracted with chloroform. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated. The resulting residue was dissolved in THF (20 mL), and the mixture was stirred at room temperature for 3 hours after adding a 2.0 mol/L ethylamine/THF solution (12.7 mL, 25.4 mmol). The reaction mixture was concentrated under reduced pressure, purified by silica gel column chromatography, and crystallized from ethanol/diethyl ether to give the title compound (Compound 1) (0.620 g, 67%).

Workup

  1. extractionthe mixture was extracted with chloroform
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. dissolutionThe resulting residue was dissolved in THF (20 mL)
  6. stirringthe mixture was stirred at room temperature for 3 hours
  7. concentrationThe reaction mixture was concentrated under reduced pressure
  8. custompurified by silica gel column chromatography
  9. customcrystallized from ethanol/diethyl ether

Sources & evidence

ORD record
ord-8c999d7c539544d0a5626b0fa83e528f
Source dataset
uspto-grants-2011_08
Patent number
US07998954B2

Reaction notes

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