m-Chloroperbenzoic acid → HCID 67350507, compound

HRID 1672764Notes

Reaction equation

HRID 1672764 reaction equation
CS[C:3]1[N:4]=[CH:5][C:6]2[C:15](=[O:16])[N:14]([CH2:17][CH:18]3[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH2:19]3)[CH2:13][C@H:12]3[N:8]([CH2:9][CH2:10][CH2:11]3)[C:7]=2[N:31]=1.ClC1C=CC=C(C(OO)=O)C=1.C(=O)(O)[O-].[Na+].[CH2:48]([NH2:50])[CH3:49].C1COCC1>ClCCl.C1COCC1>[CH2:48]([NH:50][C:3]1[N:4]=[CH:5][C:6]2[C:15](=[O:16])[N:14]([CH2:17][CH:18]3[CH2:19][CH2:20][N:21]([C:24]([O:26][C:27]([CH3:29])([CH3:28])[CH3:30])=[O:25])[CH2:22][CH2:23]3)[CH2:13][C@H:12]3[N:8]([CH2:9][CH2:10][CH2:11]3)[C:7]=2[N:31]=1)[CH3:49]

Participants

7

Reactant 4

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 66726184Ethylamine tetrahydrofuranHCID 67351756HCID 67351756, compound

Product 1

HCID 67350507HCID 67350507, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

(S)-9-Methylthio-5-(1-tert-butoxycarbonylpiperidin-4-yl)methyl-1,2,3,3a,4,5-hexahydro-5,8,10,10b-tetraazabenzo[e]azulen-6-one (2.51 g, 5.61 mmol) obtained in Step 1 was dissolved in dichloromethane (40 mL), and the mixture was stirred at room temperature for 20 minutes after adding 3-chloroperbenzoic acid (65%; 1.94 g, 7.29 mmol). Thereafter, an aqueous sodium bicarbonate solution was added to the reaction mixture, and the mixture was extracted three times with chloroform. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The residue obtained upon concentration under reduced pressure was dissolved in THF (10 mL), and the mixture was stirred overnight after adding a 2.0 mol/L ethylamine/THF solution (14.0 mL, 28.1 mmol). The residue obtained by concentrating the reaction mixture under reduced pressure was purified by silica gel column chromatography to give the title compound (Compound 23) (2.09 g, 84%) as a yellow oily substance.

Workup

  1. extractionthe mixture was extracted three times with chloroform
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe residue obtained upon concentration under reduced pressure
  5. stirringthe mixture was stirred overnight
  6. customThe residue obtained
  7. concentrationby concentrating the reaction mixture under reduced pressure
  8. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-91f546ff49954e18855781fc796bcc41
Source dataset
uspto-grants-2011_08
Patent number
US07998954B2

Reaction notes

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