Chloroacetyl chloride → HCID 178501221, compound

HRID 16707Notes

Reaction equation

HRID 16707 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][NH:11][C@H:12]1[CH2:17][CH2:16][C@H:15]([C:18]([O:20][CH3:21])=[O:19])[CH2:14][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[Cl:29][CH2:30][C:31](Cl)=[O:32].C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][N:11]([C:31](=[O:32])[CH2:30][Cl:29])[C@H:12]1[CH2:17][CH2:16][C@H:15]([C:18]([O:20][CH3:21])=[O:19])[CH2:14][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 6577Chloroacetyl chloride2×HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 178501220HCID 178501220, compound

Product 1

HCID 178501221HCID 178501221, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Methyl trans-4-({2-[(t-butoxycarbonyl)amino]ethyl}amino)-cyclohexanecarboxylate (785 mg) obtained in Reference Example 71 (1) is dissolved in chloroform (8 ml), and thereto are added triethylamine (1.82 ml) and chloroacetyl chloride (249 μl) under ice-cooling. The mixture is then stirred at room temperature for 2 hours. The reaction solution is cooled with ice again, and chloroacetyl chloride (62 μl) is supplied thereto. The mixture is stirred at room temperature for 1 hour. To the reaction solution, saturated aqueous sodium hydrogen carbonate solution is poured and the mixture is extracted with chloroform. The organic layer is washed with water and saturated brine successively, dried over sodium sulfate and evaporated to remove the solvent under reduced pressure. The resulting residue is purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=2/1, followed by 1/1) to give methyl trans-4-[{2-[(t-butoxycarbonyl)amino]ethyl}-(chloroacetyl)amino]cyclohexanecarboxylate (568 mg).

Workup

  1. temperaturecooling
  2. temperatureThe reaction solution is cooled with ice again
  3. stirringThe mixture is stirred at room temperature for 1 hour
  4. extractionthe mixture is extracted with chloroform
  5. washThe organic layer is washed with water and saturated brine successively
  6. dry with materialdried over sodium sulfate
  7. customevaporated
  8. customto remove the solvent under reduced pressure
  9. customThe resulting residue is purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=2/1, followed by 1/1)

Sources & evidence

ORD record
ord-ef34901f31c64bdc911575549f6a10f3
Source dataset
uspto-grants-2010_06
Patent number
US07737161B2

Reaction notes

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