Sodium Cyanide → HCID 68703981, compound

HRID 2201966Notes

Reaction equation

HRID 2201966 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([CH2:10][CH2:11][CH2:12][C@H:13]2[CH2:17][CH2:16][C:15](OS(C(F)(F)F)(=O)=O)=[C:14]2[C:26]2[CH:31]=[CH:30][C:29]([CH:32]([O:38][CH2:39][C:40]3[CH:45]=[CH:44][C:43]([O:46][CH3:47])=[CH:42][CH:41]=3)[CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])=[CH:28][CH:27]=2)=[CH:8][CH:9]=1)=[O:4].[C-:48]#[N:49].[Na+]>CC#N.[Cu]I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([CH2:10][CH2:11][CH2:12][C@H:13]2[CH2:17][CH2:16][C:15]([C:48]#[N:49])=[C:14]2[C:26]2[CH:27]=[CH:28][C:29]([CH:32]([O:38][CH2:39][C:40]3[CH:45]=[CH:44][C:43]([O:46][CH3:47])=[CH:42][CH:41]=3)[CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])=[CH:30][CH:31]=2)=[CH:8][CH:9]=1)=[O:4]

Participants

6

Reactant 2

HCID 8929Sodium CyanideHCID 86642145HCID 86642145, compound

Product 1

HCID 68703981HCID 68703981, compoundYield 88%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

A solution of vinyl triflate 48 (61 mg, 0.088 mmol) in 1 mL CH3CN was cannula transferred to a flask containing NaCN (21 mg, 0.42 mmol, dried under vacuum at 105° C. over 3 days), CuI (13 mg, 0.069 mmol), and (Ph3P)4Pd (8 mg, 0.0066 mmol), rinsing with 1 mL CH3CN. The reaction was stirred at 90° C. for 2 h, cooled to room temperature and then filtered through Celite, washing with ethyl acetate. The filterate was washed with 20 mL water and 20 mL brine and then was dried (Na2SO4), filtered and evaporated. The residue was purified on a Combiflash unit by Teledyne Isco (4 g silica gel column, 0%→50% ethyl acetate/hexanes) to give the title compound (41 mg, 88%).

Workup

  1. customtransferred to a flask
  2. washrinsing with 1 mL CH3CN
  3. temperaturecooled to room temperature
  4. filtrationfiltered through Celite
  5. washwashing with ethyl acetate
  6. washThe filterate was washed with 20 mL water and 20 mL brine
  7. dry with materialwas dried (Na2SO4)
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue was purified on a Combiflash unit by Teledyne Isco (4 g silica gel column, 0%→50% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-c9b9b45e13bc4d5a990885e0e58d8deb
Source dataset
uspto-grants-2016_06
Patent number
US09365485B2

Reaction notes

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