Chloroform → HCID 23084074, compound

HRID 1162336Notes

Reaction equation

HRID 1162336 reaction equation
O[CH2:2][CH2:3][N:4]([C:18]([C:20]1[NH:24][C:23]([CH3:25])=[N:22][CH:21]=1)=[O:19])[CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1.C(N(CC)CC)C.CS(Cl)(=O)=O.C(Cl)(Cl)Cl>C1COCC1.O>[CH3:25][C:23]1[N:24]2[CH2:2][CH2:3][N:4]([CH:5]3[CH2:6][CH2:7][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:15])[CH3:16])=[O:12])[CH2:9][CH2:10]3)[C:18](=[O:19])[C:20]2=[CH:21][N:22]=1

Participants

7

Reactant 4

HCID 6212ChloroformHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 23138382HCID 23138382, compound

Product 1

HCID 23084074HCID 23084074, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

tert-Butyl 4-((2-hydroxyethyl)((2-methyl-1H-imidazol-5-yl)carbonyl)amino)-1-piperidinecarboxylate (0.94 g) obtained in Example 91b) and triethylamine (0.72 ml) were dissolved in THF (30 ml). Methanesulfonic acid chloride (0.24 ml) was added dropwise under ice-cooling, and then mixed at room temperature for 3 hours. To the reaction solution were added chloroform and water, and the organic layer was collected by separation and dried over anhydrous magnesium sulfate. Then, the solvent was distilled off under reduced pressure, and the residue was purified with basic silica gel column (ethyl acetate:ethanol=5:1) to obtain the title compound as a colorless solid (0.39 g, 44%).

Workup

  1. temperaturecooling
  2. additionmixed at room temperature for 3 hours
  3. customthe organic layer was collected by separation
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThen, the solvent was distilled off under reduced pressure
  6. customthe residue was purified with basic silica gel column (ethyl acetate:ethanol=5:1)

Sources & evidence

ORD record
ord-01cc56bf466549d8a5c433c9f91854b7
Source dataset
uspto-grants-2010_10
Patent number
US07820673B2

Reaction notes

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