m-Chloroperbenzoic acid → HCID 86643706, compound

HRID 1672843Notes

Reaction equation

HRID 1672843 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[C:16]([N:20]3[CH2:29][C@H:28]4[N:24]([CH2:25][CH2:26][CH2:27]4)[C:23]4[N:30]=[C:31](SC)[N:32]=[CH:33][C:22]=4[C:21]3=[O:36])[CH:17]=[CH:18][CH:19]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].ClC1C=CC=C(C(OO)=[O:45])C=1.C(=O)(O)[O-].[Na+].[CH2:53]([NH2:55])[CH3:54].C1COCC1>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N+:11]([O-:45])([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N:20]3[CH2:29][C@H:28]4[N:24]([CH2:25][CH2:26][CH2:27]4)[C:23]4[N:30]=[C:31]([NH:55][CH2:53][CH3:54])[N:32]=[CH:33][C:22]=4[C:21]3=[O:36])[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 66726184Ethylamine tetrahydrofuranHCID 67352289HCID 67352289, compound

Product 1

HCID 86643706HCID 86643706, compoundYield 58.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-5-[3-(4-Tert-butoxycarbonylpiperazine-1-yl)phenyl]-9-methylthio-1,2,3,3a,4,5-hexahydro-5,8,10,10b-tetraazabenzo[e]azulen-6-one (0.560 g, 1.097 mmol) obtained in Step 1 was dissolved in dichloromethane (10 mL), and the mixture was stirred at room temperature for 30 minutes after adding 3-chloroperbenzoic acid (65%, 0.873 g, 3.29 mmol). A saturated aqueous sodium bicarbonate solution was added to the mixture, and the mixture was extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was dissolved in THF (5 mL), and the mixture was stirred at room temperature for 3 hours after adding a 2.0 mol/L ethylamine/THF solution (5.5 mL, 11.0 mmol). The mixture was concentrated, and the resulting residue was purified by silica gel column chromatography to give (S)-4-tert-butoxycarbonyl-1-[3-(9-ethylamino-6-oxo-2,3,3a,4-tetrahydro-1H,6H-5,8,10,10b-tetraazabenzo[e]azulen-5-yl)phenyl]piperazine-1-oxide (0.338 g, 54%).

Workup

  1. extractionthe mixture was extracted with chloroform
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe resulting residue was dissolved in THF (5 mL)
  5. stirringthe mixture was stirred at room temperature for 3 hours
  6. concentrationThe mixture was concentrated
  7. customthe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-4798ba851be44608acc46793a35e3359
Source dataset
uspto-grants-2011_08
Patent number
US07998954B2

Reaction notes

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