Hydrochloric Acid → HCID 21088561, Verbindung

HRID 350753Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 350753
Cl.[F:2][C:3]([P:12](=[O:19])([O:16][CH2:17][CH3:18])[O:13][CH2:14][CH3:15])([F:11])[C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[CH:6][CH:5]=1.[N:20]1([C:29]2[O:30][C:31]([CH2:41][CH2:42][C:43](O)=[O:44])=[C:32]([C:34]3[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][CH:35]=3)[N:33]=2)[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[N:22]=[CH:21]1.ON1C2N=CC=CC=2N=N1.C(N=C=NCCCN(C)C)C.Cl>CN(C)C=O>[N:20]1([C:29]2[O:30][C:31]([CH2:41][CH2:42][C:43]([NH:10][C:7]3[CH:8]=[CH:9][C:4]([C:3]([P:12]([O:16][CH2:17][CH3:18])([O:13][CH2:14][CH3:15])=[O:19])([F:2])[F:11])=[CH:5][CH:6]=3)=[O:44])=[C:32]([C:34]3[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][CH:35]=3)[N:33]=2)[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[N:22]=[CH:21]1

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 181649HOAtHCID 21088585HCID 21088585, VerbindungHCID 21088749HCID 21088749, Verbindung

Produkt 1

HCID 21088561HCID 21088561, VerbindungAusbeute 100,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of the obtained hydrochloride (100 mg), 3-{3-[2-(1H-benzoimidazol-1-yl)-4-(4-chlorophenyl)-5-oxazolyl]propionic acid (30 mg), 1-hydroxy-7-aza-1H-1,2,3-benzotriazole (22 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (29 mg) and N,N-dimethylformamide (0.5 ml) was stirred overnight at room temperature. To the reaction mixture was added 0.1N aqueous hydrochloric acid solution (1 ml) and the reaction mixture was extracted with ethyl acetate (2 ml). The organic layer was concentrated, introduced into preparative HPLC and purified to give 3-[2-(1H-benzoimidazol-1-yl)-4-(4-chlorophenyl)-5-oxazolyl]-N-{4-[(diethylphosphono)(difluoro)methyl]phenyl}propionamide (51.4 mg, yield 50%). Recrystallization from ethyl acetate-isopropyl ether gave yellow prism crystals. melting point: 155–156° C.

Aufarbeitung

  1. extractionthe reaction mixture was extracted with ethyl acetate (2 ml)
  2. concentrationThe organic layer was concentrated
  3. additionintroduced into preparative HPLC
  4. custompurified

Quellen und Nachweise

ORD-Eintrag
ord-8cc8cd06b1f34909b8eae18a7d4a2930
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07183276B2

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