N-Hydroxyacetamidine → (3EZ,5S)-1-[(2'-chloro 1,1'-biphenyl-4-yl)carbonyl]-5-(3-methyl-1,2,4-oxadiazol-5-yl)-3-pyrrolidinone O-methyloxime

HRID 1242556

Reaktionsgleichung

Reaktionsgleichung von HRID 1242556
C(O[C:6]([N:8]1[CH2:12][C:11](=[N:13][O:14][CH3:15])[CH2:10][C@H:9]1[C:16]([OH:18])=O)=[O:7])(C)(C)C.[C:19](=[N:22]O)([NH2:21])[CH3:20].[Cl:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[C:31]1[CH:36]=[CH:35][C:34](C(O)=O)=[CH:33][CH:32]=1.CC1C=CC=CC=1C1C=CC(C(O)=O)=CC=1>>[CH3:15][O:14][N:13]=[C:11]1[CH2:10][C@@H:9]([C:16]2[O:18][N:22]=[C:19]([CH3:20])[N:21]=2)[N:8]([C:6]([C:34]2[CH:33]=[CH:32][C:31]([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=3[Cl:24])=[CH:36][CH:35]=2)=[O:7])[CH2:12]1

Komponenten

5

Edukt 4

HCID 30926N-Hydroxyacetamidine2×HCID 160722F 1893HCID 27598152'-Methyl-biphenyl-4-carboxylic acidHCID 58714586(2S,4EZ)-1(tert-butoxycarbonyl)-4-(methoxyimino)-2-pyrrolidinecarboxylic acid2×

Produkt 1

HCID 58714521(3EZ,5S)-1-[(2'-chloro 1,1'-biphenyl-4-yl)carbonyl]-5-(3-methyl-1,2,4-oxadiazol-5-yl)-3-pyrrolidinone O-methyloximeAusbeute 31 %

Versuchsvorschrift

Following the general methods as outlined in Example 1 (Method B), starting from (2S,4EZ)-1-(tert-butoxycarbonyl)-4-(methoxyimino)-2-pyrrolidine-carboxylic acid (Intermediate 2), N′-hydroxyethanimidamide (Intermediate 7) and 2′-chloro[1,1′-biphenyl]-4-carboxylic acid (Intermediate 10), the title compound was isolated, after flash-chromatography, as a mixture of E-/Z-isomers as an oil in 31% yield (98.5% purity by HPLC).

Quellen und Nachweise

ORD-Eintrag
ord-5ca02eb674b04e83a1b1ea79c70f3835
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07115639B2

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