Methyl iodide → Methyl 1-((tert-butoxycarbonyl)amino)-4-oxocyclohexanecarboxylate

HRID 1619495Notes

Reaction equation

HRID 1619495 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].CI.[C:9]([O:13][C:14]([NH:16][C:17]1([C:24]([OH:26])=[O:25])[CH2:22][CH2:21][C:20](=[O:23])[CH2:19][CH2:18]1)=[O:15])([CH3:12])([CH3:11])[CH3:10]>CN(C)C=O>[C:9]([O:13][C:14]([NH:16][C:17]1([C:24]([O:26][CH3:1])=[O:25])[CH2:22][CH2:21][C:20](=[O:23])[CH2:19][CH2:18]1)=[O:15])([CH3:12])([CH3:10])[CH3:11]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 247297681-(((Tert-butoxy)carbonyl)amino)-4-oxocyclohexane-1-carboxylic acid

Product 1

HCID 57190358Methyl 1-((tert-butoxycarbonyl)amino)-4-oxocyclohexanecarboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3.90 g potassium carbonate and 1.30 ml methyl iodide are added to 4.65 g 1-tert.-butoxycarbonylamino-4-oxo-cyclohexanecarboxylic acid in 45 ml N,N-dimethylformamide and the reaction mixture is stirred for three hours at ambient temperature. Then the solvent is distilled off using the rotary evaporator and the residue is divided between 10% potassium carbonate solution and diethyl ether. The aqueous phase is separated off and extracted with diethyl ether and the combined organic phases are washed with saturated sodium chloride solution, dried on magnesium sulphate and evaporated down. A colourless oil is left, which slowly crystallises.

Workup

  1. distillationThen the solvent is distilled off
  2. customthe rotary evaporator
  3. customThe aqueous phase is separated off
  4. extractionextracted with diethyl ether
  5. washthe combined organic phases are washed with saturated sodium chloride solution
  6. customdried on magnesium sulphate
  7. customevaporated down
  8. waitA colourless oil is left
  9. customwhich slowly crystallises

Sources & evidence

ORD record
ord-6731bbd97cfb497199a6ba0abccd92ac
Source dataset
uspto-grants-2014_07
Patent number
US08772298B2

Reaction notes

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