Hydrochloric Acid → HCID 86597662, Verbindung

HRID 350754Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 350754
[NH2:1][C:2]1[CH:17]=[CH:16][C:5]([CH:6]([P:8](=[O:15])([O:12][CH2:13][CH3:14])[O:9][CH2:10][CH3:11])[OH:7])=[CH:4][CH:3]=1.[N:18]1([C:27]2[O:28][C:29]([CH2:39][CH2:40][C:41](O)=[O:42])=[C:30]([C:32]3[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=3)[N:31]=2)[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2[N:20]=[CH:19]1.ON1C2N=CC=CC=2N=N1.C(N=C=NCCCN(C)C)C.Cl>CN(C)C=O>[N:18]1([C:27]2[O:28][C:29]([CH2:39][CH2:40][C:41]([NH:1][C:2]3[CH:3]=[CH:4][C:5]([CH:6]([P:8]([O:9][CH2:10][CH3:11])([O:12][CH2:13][CH3:14])=[O:15])[OH:7])=[CH:16][CH:17]=3)=[O:42])=[C:30]([C:32]3[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=3)[N:31]=2)[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2[N:20]=[CH:19]1

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 181649HOAtHCID 21088585HCID 21088585, VerbindungHCID 23061737Diethyl P-[(4-aminophenyl)hydroxymethyl]phosphonate

Produkt 1

HCID 86597662HCID 86597662, VerbindungAusbeute 58,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of diethyl 4-amino-α-hydroxybenzylphosphonate (50 mg), 3-{3-[2-(1H-benzoimidazol-1-yl)-4-(4-chlorophenyl)-5-oxazolyl]propionic acid (54 mg), 1-hydroxy-7-aza-1H-1,2,3-benzotriazole (38 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (43 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 (2 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)(hydroxy)methyl]phenyl}propionamide (52 mg, 58%). Recrystallization from ethyl acetate-isopropyl ether gave yellow prism crystals. melting point: 171–172° C. MS (ESI+): 609 (M+H)

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-7b4ec0dce8374ff9a23c02e94f45fe50
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07183276B2

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