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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1242556Generated: October 25, 2026

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

https://huagongshe.com/reaction/1242556

Reaction equation

Participants

RoleNameHCIDCharge
ReactantN-HydroxyacetamidineHCID 30926—
ReactantF 1893HCID 160722—
Reactant2'-Methyl-biphenyl-4-carboxylic acidHCID 2759815—
Reactant(2S,4EZ)-1(tert-butoxycarbonyl)-4-(methoxyimino)-2-pyrrolidinecarboxylic acidHCID 58714586—
Product(3EZ,5S)-1-[(2'-chloro 1,1'-biphenyl-4-yl)carbonyl]-5-(3-methyl-1,2,4-oxadiazol-5-yl)-3-pyrrolidinone O-methyloximeHCID 5871452131%

Reaction Steps

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).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07115639B2
Source datasetuspto-grants-2006_10
ORD IDord-5ca02eb674b04e83a1b1ea79c70f3835
Source noteuspto-grants-2006_10