Methyl iodide → HCID 178502272, compound

HRID 1403132Notes

Reaction equation

HRID 1403132 reaction equation
[CH3:1][O:2][C:3](=[O:27])[NH:4][C@@H:5]([CH2:23][CH2:24]SC)[C:6]([NH:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11][CH2:10]1)=[O:7].C(Cl)Cl.CI>CO>[CH3:1][O:2][C:3](=[O:27])[NH:4][C@H:5]1[CH2:23][CH2:24][N:8]([C@H:9]2[CH2:14][CH2:13][C@H:12]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11][CH2:10]2)[C:6]1=[O:7]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 6344DichloromethaneHCID 178502281HCID 178502281, compound

Product 1

HCID 178502272HCID 178502272, compoundYield 36.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of methyl[(2S)-1-({trans-4-[(tert-butoxycarbonyl)amino]cyclohexyl}amino)-4-(methylsulfanyl)-1-oxobutan-2-yl]carbamate (2.0 g), methylene chloride (20 mL) and methanol (20 mL) was added methyl iodide (15.5 mL), followed by stirring at room temperature overnight. The solvent was evaporated under reduced pressure, and to a mixture of the residue and dimethylformamide (10 mL) was added cesium carbonate (4.8 g), followed by stirring overnight. To the reaction solution was added water, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine. The organic layer was dried over anhydrous sodium sulfate, the desiccant was removed by filtration, and then the solvent was evaporated under reduced pressure. To the residue was added ethanol, and the resulting solid was collected by filtration and dried under reduced pressure to obtain methyl[(3S)-1-{trans-4-[(tert-butoxycarbonyl)amino]cyclohexyl}-2-oxopyrrolidin-3-yl]carbamate (0.65 g).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additionto a mixture of the residue and dimethylformamide (10 mL)
  3. additionwas added cesium carbonate (4.8 g)
  4. stirringby stirring overnight
  5. additionTo the reaction solution was added water
  6. extractionfollowed by extraction with ethyl acetate
  7. washThe organic layer was washed with saturated brine
  8. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  9. customthe desiccant was removed by filtration
  10. customthe solvent was evaporated under reduced pressure
  11. additionTo the residue was added ethanol
  12. filtrationthe resulting solid was collected by filtration
  13. customdried under reduced pressure

Sources & evidence

ORD record
ord-2fc4de98428d45fb9d8399ac88714eb9
Source dataset
uspto-grants-2014_12
Patent number
US08912180B2

Reaction notes

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