Acetic Acid → HCID 22479129, compound

HRID 2182592Notes

Reaction equation

HRID 2182592 reaction equation
C([C:3]1[CH:8]=[CH:7][CH:6]=C[C:4]=1[C:9]1[CH:34]=[CH:33][C:12]([CH2:13][C:14]23[C:22](=[O:23])[N:21]([C:24]4[CH:29]=[C:28]([Cl:30])[CH:27]=[C:26]([Cl:31])[CH:25]=4)[C:20](=[O:32])[N:19]2[CH2:18][CH2:17][CH2:16][CH2:15]3)=[CH:11][CH:10]=1)=O.[C-:35]#N.[Na+].[CH3:38][C:39]([OH:41])=[O:40]>CO.O=[Mn]=O>[CH3:35][O:40][C:39]([C:38]1[CH:6]=[CH:7][CH:8]=[CH:3][C:4]=1[C:9]1[CH:10]=[CH:11][C:12]([CH2:13][C:14]23[C:22](=[O:23])[N:21]([C:24]4[CH:29]=[C:28]([Cl:30])[CH:27]=[C:26]([Cl:31])[CH:25]=4)[C:20](=[O:32])[N:19]2[CH2:18][CH2:17][CH2:16][CH2:15]3)=[CH:33][CH:34]=1)=[O:41]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 8929Sodium CyanideHCID 22479142HCID 22479142, compound

Product 1

HCID 22479129HCID 22479129, compound

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of 6-[4-(2-formylphenyl)benzyl]-8-(3,5-dichlorophenyl)-1,8-diazabicyclo[4.3.0]nonane-7,9-dione (0.206 g) in MeOH (20 mL) was added NaCN (0.204 g), AcOH (0.086 mL) and MnO2 (activated, 1.84 g) and the mixture was stirred overnight at room temperature. The inorganics were removed by filtration through Celite and the filtrate was evaporated. The residue was dissolved in EtOAc and washed with water, brine, dried (MgSO4), filtered, and concentrated. Purification by chromatography (Silica gel: EtOAc/hexane: 1/2) afforded the titled compound (0.161 g). It was converted to the HCl salt. MS (m/z) 545(M++Na), 523 (MH+).

Workup

  1. customThe inorganics were removed by filtration through Celite
  2. customthe filtrate was evaporated
  3. dissolutionThe residue was dissolved in EtOAc
  4. washwashed with water, brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by chromatography (Silica gel: EtOAc/hexane: 1/2)

Sources & evidence

ORD record
ord-a2d8e3deabc149e496abcfec3e544b84
Source dataset
uspto-grants-2005_05
Patent number
US06897225B1

Reaction notes

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