Carbon Dioxide → HCID 71246792, compound

HRID 1519109Notes

Reaction equation

HRID 1519109 reaction equation
[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[NH:11][C:12](=[O:31])[C:13]([CH3:30])([N:15]([CH3:29])[S:16]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[N+:26]([O-:28])=[O:27])(=[O:18])=[O:17])[CH3:14])[CH2:8]2.[C:32](=O)=O.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.CI.[Cl-].[NH4+]>C1COCC1.CC(C)=O>[CH:1]12[CH2:8][CH:7]3[CH2:6][CH:5]([CH2:4][CH:3]([CH2:9]3)[CH:2]1[NH:11][C:12](=[O:31])[C:13]([CH3:14])([N:15]([CH3:29])[S:16]([CH:19]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[N+:26]([O-:28])=[O:27])[CH3:32])(=[O:18])=[O:17])[CH3:30])[CH2:10]2

Participants

8

Reactant 5

HCID 280Carbon DioxideHCID 6328Methyl iodideHCID 25517Ammonium ChlorideHCID 2733832Lithium HexamethyldisilazideHCID 71246887HCID 71246887, compound

Product 1

HCID 71246792HCID 71246792, compoundYield 19%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-70 °C

Procedure

N-(adamantane-2-yl)-2-methyl-2-(N-methyl-1-(2-nitrophenyl)methylsulfonamido)propanamide (100 mg, 0.23 mmol) was dissolved in THF (2 ml), and cooled to −70° C. by using Dry ice and acetone. 1M LiHMDS (0.46 ml, 0.46 mmol) in THF was added thereto, followed by stirring for 1 hour at −70° C. Then, the temperature was raised up to −40° C., and MeI (0.143 ml, 2.3 mmol) was added thereto, followed by stirring at room temperature for 4 hours. After the stirring for 4 hours, ammonium chloride solution (4 ml) was added thereto to quench the reaction. The organic layer was washed with ammonium chloride solution (4 ml) twice, and separated. The separated organic layer was dried with MgSO4, and filtered. Through vacuum distillation, the solvent was removed, and through column chromatography, N-(adamantane-2-yl)-2-methyl-2-(N-methyl-1-(2-nitrophenyl)ethylsulfonamido)propanamide (21 mg, 0.11 mmol, 19%) was obtained.

Workup

  1. additionwas added
  2. stirringby stirring at room temperature for 4 hours
  3. waitAfter the stirring for 4 hours
  4. customto quench
  5. customthe reaction
  6. washThe organic layer was washed with ammonium chloride solution (4 ml) twice
  7. customseparated
  8. dry with materialThe separated organic layer was dried with MgSO4
  9. filtrationfiltered
  10. distillationThrough vacuum distillation
  11. customthe solvent was removed

Sources & evidence

ORD record
ord-4c27d4da08e848ebbeeebe458dee376a
Source dataset
uspto-grants-2015_07
Patent number
US09073830B2

Reaction notes

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