4-Phenylbenzoyl chloride → (3Ez,5s)-5-(3-benzyl-1,2,4-oxadiazol-5-yl)-1-([1,1'-biphenyl]-4-ylcarbonyl)-3-pyrrolidinone o-methyloxime

HRID 1242603

Reaktionsgleichung

Reaktionsgleichung von HRID 1242603
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]1([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:24]=[CH:23][C:22](C(Cl)=O)=[CH:21][CH:20]=1.O[N:35]=[C:36]([NH2:44])[CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>>[CH3:15][O:14][N:13]=[C:11]1[CH2:10][C@@H:9]([C:16]2[O:18][N:44]=[C:36]([CH2:37][C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[N:35]=2)[N:8]([C:6]([C:31]2[CH:30]=[CH:29][C:28]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)=[CH:33][CH:32]=2)=[O:7])[CH2:12]1

Komponenten

4

Edukt 3

HCID 841514-Phenylbenzoyl chlorideHCID 2731007N'-hydroxy-2-phenylethanimidamideHCID 58714586(2S,4EZ)-1(tert-butoxycarbonyl)-4-(methoxyimino)-2-pyrrolidinecarboxylic acid2×

Produkt 1

HCID 58714553(3Ez,5s)-5-(3-benzyl-1,2,4-oxadiazol-5-yl)-1-([1,1'-biphenyl]-4-ylcarbonyl)-3-pyrrolidinone o-methyloxime

Versuchsvorschrift

Following the general method as outlined in Example 59, starting from (2S,4EZ)-1-(tert-butoxycarbonyl)-4-(methoxyimino)-2-pyrrolidine-carboxylic acid (Intermediate 2), [1,1′-biphenyl]-4-carbonyl chloride, and N′-hydroxy-2-phenylethanimidamide, the title compound was obtained in 86% purity by HPLC. MS(ESI+): m/z=453.2.

Quellen und Nachweise

ORD-Eintrag
ord-11d61133ed054ed49c010183c59fd962
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07115639B2

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