2-Phenylbutyric Acid → Methyl 3-methoxy-4-[6-(2-phenylbutanamido)benzimidazol-1-ylmethyl]benzoate

HRID 1723222Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1723222
C(N1C=CN=C1)(N1C=CN=C1)=O.[C:13]1([CH:19]([CH2:23][CH3:24])[C:20]([OH:22])=O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[NH2:25][C:26]1[CH:27]=[CH:28][C:29]2[N:33]=[CH:32][N:31]([CH2:34][C:35]3[CH:44]=[CH:43][C:38]([C:39]([O:41][CH3:42])=[O:40])=[CH:37][C:36]=3[O:45][CH3:46])[C:30]=2[CH:47]=1>ClCCl>[CH3:46][O:45][C:36]1[CH:37]=[C:38]([CH:43]=[CH:44][C:35]=1[CH2:34][N:31]1[C:30]2[CH:47]=[C:26]([NH:25][C:20](=[O:22])[CH:19]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:23][CH3:24])[CH:27]=[CH:28][C:29]=2[N:33]=[CH:32]1)[C:39]([O:41][CH3:42])=[O:40]

Komponenten

5

Edukt 3

HCID 70122-Phenylbutyric AcidHCID 682631,1'-CarbonyldiimidazoleHCID 14763098Methyl 4-(6-aminobenzimidazol-1-ylmethyl)-3-methoxybenzoate

Produkt 1

HCID 23365891Methyl 3-methoxy-4-[6-(2-phenylbutanamido)benzimidazol-1-ylmethyl]benzoateAusbeute 25 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel3×

Versuchsvorschrift

A solution of 1,1'-carbonyldiimidazole (0.23 g.) and 2-phenylbutyric acid (0.22 g.) in dichloromethane (3 ml.) was heated under reflux for 30 minutes and then treated with a solution of (J) (0.41 g.) in dichloromethane (3 ml.). The mixture was heated under reflux for an additional 10 minutes and then diluted with dichloromethane. This mixture was washed successively with 10% v/v hydrochloric acid, water, and brine, then dried (MgSO4) and evaporated. The resultant residue was purified by flash chromatography on a 5×25 cm. silica gel column using 3:97 v/v methanol:dichloromethane as the eluent to give the title compound (0.15 g., 25%): partial NMR: 2.0(br m,2H, CH3CH2), 3.4(t,1H, CH2CH), 7.3(s,5H, Ar).

Aufarbeitung

  1. temperatureunder reflux for 30 minutes
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for an additional 10 minutes
  4. washThis mixture was washed successively with 10% v/v hydrochloric acid, water, and brine
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe resultant residue was purified by flash chromatography on a 5×25 cm

Quellen und Nachweise

ORD-Eintrag
ord-ab0af418cc8f411a9072a4e33e9c1ef6
Quelldatensatz
uspto-grants-1989_08
Patentnummer
US04859692

Notizen zur Reaktion

Wird geladen…