2-Chlorophenyl-(6,7-dihydro-4H-thieno[3,2-c]pyridin-5-yl)acetamide → (S)-2-(2-chloro-phenyl)(4,5,6,7-tetrahydrothieno[3,2-c]pyrid-5-yl)acetamide (+)-camphor sulfonic acid salt

HRID 988851Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 988851
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([N:12]1[CH2:17][CH2:16][C:15]2[S:18][CH:19]=[CH:20][C:14]=2[CH2:13]1)[C:9]([NH2:11])=[O:10].O.[C:22]12([CH2:32][S:33]([OH:36])(=[O:35])=[O:34])[C:29]([CH3:31])([CH3:30])[CH:26]([CH2:27][CH2:28]1)[CH2:25][C:23]2=[O:24]>CC(C)=O>[C:22]12([CH2:32][S:33]([OH:36])(=[O:34])=[O:35])[C:29]([CH3:31])([CH3:30])[CH:26]([CH2:27][CH2:28]1)[CH2:25][C:23]2=[O:24].[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C@H:8]([N:12]1[CH2:17][CH2:16][C:15]2[S:18][CH:19]=[CH:20][C:14]=2[CH2:13]1)[C:9]([NH2:11])=[O:10]

Komponenten

4

Edukt 2

HCID 113128242-Chlorophenyl-(6,7-dihydro-4H-thieno[3,2-c]pyridin-5-yl)acetamideHCID 1226536210-Camphorsulfonic acid monohydrate

Produkt 1

HCID 131724104(S)-2-(2-chloro-phenyl)(4,5,6,7-tetrahydrothieno[3,2-c]pyrid-5-yl)acetamide (+)-camphor sulfonic acid saltAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

A solution of 5 g (16.31 mmol) of (±)-(2-chloro-phenyl)-(6,7-dihydro-4H-thieno[3,2-c]pyrid-5-yl)acetamide (prepared as given in Examples 10-15) and 4.15 g (16.2 mmol) (1S) (+)-camphor-10-sulphonic acid monohydrate in 100 mL acetone was stirred at room temperature for 20 h. Subsequently it was kept for 1 week in a freezer. Few crystals appeared concentration of volume by evaporating solvent under reduced pressure and repeated recrystallization in freezer for few days gave 3.3 g (75% yield) of (S)-2-(2-chloro-phenyl)-(4,5,6,7-tetrahydrothieno[3,2-c]pyrid-5-yl)acetamide (+)-camphor sulfonic acid salt. The salt was further purified by recrystallization in acetone, until constant specific optical rotation was obtained.

Aufarbeitung

  1. waitSubsequently it was kept for 1 week in a freezer
  2. customby evaporating solvent under reduced pressure
  3. customrecrystallization in freezer for few days

Quellen und Nachweise

ORD-Eintrag
ord-74af714cf715486fbbace01793ffc93f
Quelldatensatz
uspto-grants-2003_10
Patentnummer
US06635763B2

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