Potassium Iodide → HCID 10588819, compound

HRID 2184998Notes

Reaction equation

HRID 2184998 reaction equation
CC1C=CC(S(O[CH2:12][C@H:13]([NH:20][C:21]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:22])[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(=O)=O)=CC=1.[C-:31]#[N:32].[K+].C1OCCOCCOCCOCCOCCOC1.[I-].[K+]>CN(C=O)C>[CH2:24]([O:23][C:21]([NH:20][C@H:13]([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[CH2:12][C:31]#[N:32])=[O:22])[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 9032Potassium CyanideHCID 2855718-Crown-6HCID 10788517HCID 10788517, compound

Product 1

HCID 10588819HCID 10588819, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

60.5 g of (R)-2-benzyloxycarbonylamino-2-phenylethyl 4-methylphenylsulfonate (142.2 mmol) were dissolved in 675 ml of DMF. 13.9 g of potassium cyanide (213.3 mmol), 5.64 g of 18-crown-6 (21.33 mmol) and 520 mg of potassium iodide (3.13 mmol) were added and the mixture was stirred at 50° C. for 20 hours. The reaction solution was poured into 500 ml of ice water and then stirred at 0° C. for 5 hours. The precipitate was filtered off with suction and dissolved in ethyl acetate. The organic phase was washed three times with water, dried over magnesium sulfate and concentrated in vacuo. The residue was triturated with diethyl ether, filtered off with suction, washed with diethyl ether and dried over phosphorus pentoxide. Yield: 25.3 g (63.5%).

Workup

  1. stirringstirred at 0° C. for 5 hours
  2. filtrationThe precipitate was filtered off with suction
  3. dissolutiondissolved in ethyl acetate
  4. washThe organic phase was washed three times with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was triturated with diethyl ether
  8. filtrationfiltered off with suction
  9. washwashed with diethyl ether
  10. dry with materialdried over phosphorus pentoxide

Sources & evidence

ORD record
ord-3a3dc8d876ae45fa8deb94006cf1413a
Source dataset
uspto-grants-2002_06
Patent number
US06399643B1

Reaction notes

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