Hydrochloric Acid → (4S,5R)-N-benzyl-4,5-diphenyl-4,5-dihydro-1H-imidazol-2-amine;hydrochloride

HRID 2053519Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2053519
[ClH:1].C(OC([N:9]1[C@H:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C@H:12]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:11]=[C:10]1[NH:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=O)(C)(C)C>CCOC(C)=O>[ClH:1].[C:14]1([C@H:13]2[C@@H:12]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[NH:11][C:10]([NH:26][CH2:27][C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)=[N:9]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 68567154tert-butyl (4S,5R)-2-(benzylamino)-4,5-diphenyl-4,5-dihydroimidazole-1-carboxylate

Produkt 1

HCID 68570665(4S,5R)-N-benzyl-4,5-diphenyl-4,5-dihydro-1H-imidazol-2-amine;hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Hydrogen chloride is bubbled into a solution of 77 (200 mg, 0.47 mmol) in EtOAc (10 mL) for 1 min, and the solution is stirred at RT overnight. The solvent is removed by rotary evaporation, and the residue is crystallized from dichloromethane and Et2O to give 130 mg of the product 78. 1H NMR (DMSO-d6) δ 9.80-8.30 (m, 3H), 7.60-7.30 (m, 5H), 7.20-7.00 (m, 6H), 7.00-6.85 (m, 4H), 5.49 (s, 2H), 4.59 (d, 2H); MS: m/z 328 (M++1).

Aufarbeitung

  1. customThe solvent is removed by rotary evaporation
  2. customthe residue is crystallized from dichloromethane and Et2O

Quellen und Nachweise

ORD-Eintrag
ord-149f2287fcb84cf9b32d5bb2b6110a93
Quelldatensatz
uspto-grants-2008_02
Patentnummer
US07326792B2

Notizen zur Reaktion

Wird geladen…