Potassium Cyanide → N-(4-iso-propylbenzenesulfonyl)-alpha-(4-cyanomethyl-2-n-propylphenoxy)-3,4-methylenedioxyphenylacetamide

HRID 865537Notes

Reaction equation

HRID 865537 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][C:14](=[O:37])[CH:15]([C:28]2[CH:33]=[CH:32][C:31]3[O:34][CH2:35][O:36][C:30]=3[CH:29]=2)[O:16][C:17]2[CH:22]=[CH:21][C:20]([CH2:23]Br)=[CH:19][C:18]=2[CH2:25][CH2:26][CH3:27])(=[O:12])=[O:11])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[C-:38]#[N:39].[K+].C(Cl)(Cl)Cl.CO.[NH4+].[OH-]>CS(C)=O.CCOC(C)=O.OS([O-])(=O)=O.[Na+]>[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][C:14](=[O:37])[CH:15]([C:28]2[CH:33]=[CH:32][C:31]3[O:34][CH2:35][O:36][C:30]=3[CH:29]=2)[O:16][C:17]2[CH:22]=[CH:21][C:20]([CH2:23][C:38]#[N:39])=[CH:19][C:18]=2[CH2:25][CH2:26][CH3:27])(=[O:12])=[O:11])=[CH:6][CH:5]=1)([CH3:3])[CH3:2]

Participants

7

Reactant 3

HCID 9032Potassium CyanideHCID 21873181Chloroform methanol ammonium hydroxideHCID 22912502N-(4-iso-propylbenzenesulfonyl)-alpha-(4-bromomethyl-2-n-propylphenoxy)-3,4-methylenedioxyphenylacetamide

Product 1

HCID 22912464N-(4-iso-propylbenzenesulfonyl)-alpha-(4-cyanomethyl-2-n-propylphenoxy)-3,4-methylenedioxyphenylacetamide

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolventHCID 516919Sodium BisulfateSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of the crude product of Step A dissolved in 1.5 mL of methyl sulfoxide was added 0.050 g (0.762 mmol) of potassium cyanide at room temperature under nitrogen. The reaction mixture was stirred at room temperature for 1 h when TLC analysis (80:15:1 CHCl3 -MeOH-NH4OH) indicated that the reaction was complete. The reaction mixture was diluted with EtOAc and 10% aqueous NaHSO4 solution. The aqueous phase was separated and the EtOAc portion was washed with brine (2×10 mL). The EtOAc portion was then dried over MgSO4, filtered, evaporated to a residue, and purified. Purification was done by reversed phase HPLC (Waters Millipore Delta Prep 4000 with Delta-Pak C18 15 μm 100 A column cartridge) with a solvent system of 30:70 water-acetonitrile and 0.1% TFA buffer. The purified fractions collected were combined in a round bottom flask, frozen in a -78° C. dry ice-acetone bath, and lyophilized. The resulting lyophilized powder afforded 0.071 g (35% 2-step yield).

Workup

  1. customThe aqueous phase was separated
  2. washthe EtOAc portion was washed with brine (2×10 mL)
  3. dry with materialThe EtOAc portion was then dried over MgSO4
  4. filtrationfiltered
  5. customevaporated to a residue
  6. custompurified
  7. customPurification
  8. customThe purified fractions collected
  9. customwere combined in a round bottom flask
  10. customafforded
  11. custom0.071 g (35% 2-step yield)

Sources & evidence

ORD record
ord-fc691ededd4d4d6cb0e7c91882924941
Source dataset
uspto-grants-1996_10
Patent number
US05565485

Reaction notes

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