Carbon Disulfide → tert-butyl (2S,4EZ)-4-(methoxy-imino)-2-(5-thioxo-4,5-dihydro-1,3,4-oxadiazol-2-yl)-1-pyrrolidinecarboxylate

HRID 1242618Notes

Reaction equation

HRID 1242618 reaction equation
[NH:1]([C:3]([C@@H:5]1[CH2:9][C:8](=[N:10][O:11][CH3:12])[CH2:7][N:6]1[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[O:4])[NH2:2].[C:20](=S)=[S:21].[OH-].[K+]>C(O)C>[CH3:12][O:11][N:10]=[C:8]1[CH2:7][N:6]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C@H:5]([C:3]2[O:4][C:20](=[S:21])[NH:2][N:1]=2)[CH2:9]1

Participants

5

Reactant 3

HCID 6348Carbon DisulfideHCID 14797Potassium HydroxideHCID 58714558tert-butyl (2S,4EZ)-2-(hydrazinocarbonyl)-4-(methoxyimino)-1-pyrrolidinecarboxylate2×

Product 1

HCID 131725971tert-butyl (2S,4EZ)-4-(methoxy-imino)-2-(5-thioxo-4,5-dihydro-1,3,4-oxadiazol-2-yl)-1-pyrrolidinecarboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of tert-butyl (2S,4EZ)-2-(hydrazinocarbonyl)-4-(methoxyimino)-1-pyrrolidinecarboxylate (Intermediate 9, 2.86 mmoles; 780 mg) in ethanol (25 mL) at 0° C. was added carbon disulfide (6.86 mmoles; 522 mg) and potassium hydroxide (3 mmoles; 168 mg). The mixture was refluxed for 7 h. The solvent was evaporated and the residue re-dissolved in EtOAc and washed with NH4Cl sat and 10% NaHCO3 and brine. The organic layer was dried over Na2SO4 and evaporated to give the desired N-protected intermediate, tert-butyl (2S,4EZ)-4-(methoxyimino)-2-(5-thioxo-4,5-dihydro-1,3,4-oxadiazol-2-yl)-1-pyrrolidine-carboxylate, as a yellowish oil (200 mg, 23%).

Workup

  1. temperatureThe mixture was refluxed for 7 h
  2. customThe solvent was evaporated
  3. dissolutionthe residue re-dissolved in EtOAc
  4. washwashed with NH4Cl
  5. dry with materialThe organic layer was dried over Na2SO4
  6. customevaporated

Sources & evidence

ORD record
ord-caac2c05ef024598bc28c95dc461eafa
Source dataset
uspto-grants-2006_10
Patent number
US07115639B2

Reaction notes

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