Methyl iodide → HCID 68454645, compound

HRID 502413Notes

Reaction equation

HRID 502413 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]([C:17]2[CH:18]=[N:19][C:20]([NH:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[CH:21][CH:22]=2)=[O:16])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:31][Si](C)(C)[N-][Si](C)(C)C.[Na+].CI>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]([C:17]2[CH:18]=[N:19][C:20]([N:23]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH3:31])=[CH:21][CH:22]=2)=[O:16])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 2724254Sodium bis(trimethylsilyl)amideHCID 68458458HCID 68458458, compound

Product 1

HCID 68454645HCID 68454645, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The above prepared 4-[(6-tert-butoxycarbonylamino-pyridine-3-carbonyl)-amino]-piperidine-1-carboxylic acid tert-butyl ester (0.720 g, 1.71 mmol) was dissolved in 30 ml of abs. THF and treated at 0° C. with sodium hexamethyldisilazide-solution (1M in THF, 1.05 eq.) and, after 15 Min., 50 eq. of methyl iodide (5.33 ml). The mixture was allowed to react for six days! Pouring onto crashed ice/NH4Cl, twofold extraction with AcOEt, washing with water and brine, drying over magnesium sulfate, and evaporation of the solvents, followed by flash chromatography (silica gel, hexane/AcOEt=55/45) yielded eventually 0.497 g of the title compound as white foam.

Workup

  1. dissolutionwas dissolved in 30 ml of abs
  2. customto react for six days
  3. additionPouring
  4. extractionice/NH4Cl, twofold extraction with AcOEt
  5. washwashing with water and brine
  6. dry with materialdrying over magnesium sulfate, and evaporation of the solvents

Sources & evidence

ORD record
ord-d34dd659dcb94b5889f67d5d3a6a583f
Source dataset
uspto-grants-2010_08
Patent number
US07772253B2

Reaction notes

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