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

HRID 54520ノート

反応式

HRID 54520 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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:

後処理

  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

出典と根拠

ORDレコード
ord-3cb031c71e904f7598c4f82ad9a093db
出典データセット
uspto-grants-1997_04
特許番号
US05622982

反応ノート

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