Triethylamine → 1-[(1S)-Camphanoyl]amino-1-(5-chloro-2-pyridyl)-2-(1H-imidazol-1-yl)ethane

HRID 54520Notes

Reaction equation

HRID 54520 reaction equation
[NH2:1][CH:2]([C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][N:10]=1)[CH2:3][N:4]1[CH:8]=[CH:7][N:6]=[CH:5]1.C(N(CC)CC)C.[C@:23]12([CH3:35])[C:29]([CH3:31])([CH3:30])[CH:26]([CH2:27][CH2:28]1)[CH2:25][CH:24]2[C:32](Cl)=[O:33]>ClCCl>[C@:23]12([CH3:35])[C:29]([CH3:30])([CH3:31])[CH:26]([CH2:27][CH2:28]1)[CH2:25][CH:24]2[C:32]([NH:1][CH:2]([C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][N:10]=1)[CH2:3][N:4]1[CH:8]=[CH:7][N:6]=[CH:5]1)=[O:33]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 199594121-Amino-1-(5-chloro-2-pyridyl)-2-(1H-imidazol-1-yl)ethaneHCID 71432218(1s)-Camphanoyl chloride

Product 1

HCID 676173331-[(1S)-Camphanoyl]amino-1-(5-chloro-2-pyridyl)-2-(1H-imidazol-1-yl)ethane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.38 g of 1-amino-1-(5-chloro-2-pyridyl)-2-(1H-imidazol-1-yl)ethane (racemic compound, see A) above) in 4 ml of dry dichloromethane is added 0.26 g (0.36 ml) of triethylamine. The mixture is stirred and cooled to -79°. Then 0.44 g of (1S)(-)-camphanic acid chloride are added in such a way that the temperature does not exceed -74°. Stirring is continued for additionally 90 minutes without further cooling. For working up the mixture is poured onto ice-water, extracted three times with dichloromethane and washed with brine. After drying with sodium sulfate the solvent is evaporated. A mixture of the two diastereomeric amides is obtained which is separated by chromatography over silica gel (dichloromethane/methanol/heptane=10/1/5). The two compounds are obtained as white crystals:

Workup

  1. temperaturecooled to -79°
  2. customdoes not exceed -74°
  3. stirringStirring
  4. additionis poured onto ice-water
  5. extractionextracted three times with dichloromethane
  6. washwashed with brine
  7. dry with materialAfter drying with sodium sulfate the solvent
  8. customis evaporated
  9. additionA mixture of the two diastereomeric amides
  10. customis obtained which
  11. customis separated by chromatography over silica gel (dichloromethane/methanol/heptane=10/1/5)
  12. customThe two compounds are obtained as white crystals

Sources & evidence

ORD record
ord-3cb031c71e904f7598c4f82ad9a093db
Source dataset
uspto-grants-1997_04
Patent number
US05622982

Reaction notes

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