Potassium Cyanide → HCID 57208374, compound

HRID 1638179Notes

Reaction equation

HRID 1638179 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@@H:12]([C:13]2[CH:18]=[CH:17][C:16]([C:19]#[C:20][Si](C)(C)C)=[CH:15][CH:14]=2)[C@H:11]([C:25]([O:27][CH3:28])=[O:26])[O:10][C:9]1([CH3:30])[CH3:29])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C-]#N.[K+]>C(O)C.O.[N+]([O-])([O-])=O.[Ag+]>[C:1]([O:5][C:6]([N:8]1[C@@H:12]([C:13]2[CH:14]=[CH:15][C:16]([C:19]#[CH:20])=[CH:17][CH:18]=2)[C@H:11]([C:25]([O:27][CH3:28])=[O:26])[O:10][C:9]1([CH3:30])[CH3:29])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 2

HCID 9032Potassium CyanideHCID 56974792HCID 56974792, compound

Product 1

HCID 57208374HCID 57208374, compoundYield 47.2%

Reagents, catalysts & solvents 3

HCID 24470Silver NitrateCatalystHCID 702EthanolSolvent2×HCID 962WaterSolvent2×

Conditions

Temperature
20 °C

Procedure

To a solution of 1.4 g of methyl (4S,5R)-3-tert-butoxycarbonyl-2,2-dimethyl-4-(4-trimethylsilylethynylphenyl)-5-oxazolidinecarboxylate in 20 cm3 of ethanol is added dropwise, with stirring and at a temperature in the region of 20° C., a solution of 1.7 g of silver nitrate in a mixture of 2 cm3 of distilled water and 1 cm3 of ethanol. The reaction mixture is subsequently stirred for 2 hours at a temperature in the region of 20° C., followed by dropwise addition of a solution of 2.93 g of potassium cyanide in 3 cm3 of distilled water. Stirring is continued at a temperature in the region of 20° C. for 18 hours and the mixture is extracted with 3 times 50 cm3 of ethyl acetate. The organic phases are combined, washed with 3 times 5 cm3 of distilled water, dried over magnesium sulphate, filtered and then concentrated to dryness under reduced pressure (2.7 kPa) at 40° C. 0.55 g of methyl (4S,5R)-3-tert-butoxycarbonyl-2,2-dimethyl-4-(4-ethynylphenyl)-5-oxazolidinecarboxylate is thus obtained, in the form of a brown oil which is converted to the corresponding acid under the conditions described in Example 2.

Workup

  1. stirringThe reaction mixture is subsequently stirred for 2 hours at a temperature in the region of 20° C.
  2. stirringStirring
  3. extractionthe mixture is extracted with 3 times 50 cm3 of ethyl acetate
  4. washwashed with 3 times 5 cm3 of distilled water
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness under reduced pressure (2.7 kPa) at 40° C

Sources & evidence

ORD record
ord-a6442f8d98644020826af06df002e36b
Source dataset
uspto-grants-2000_03
Patent number
US06043375

Reaction notes

Loading…