HuagongsheHuagongshe Chemistry Print Report · For research reference only
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
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | N-Hydroxyacetamidine | HCID 30926 | — |
| Reactant | F 1893 | HCID 160722 | — |
| Reactant | 2'-Methyl-biphenyl-4-carboxylic acid | HCID 2759815 | — |
| Reactant | (2S,4EZ)-1(tert-butoxycarbonyl)-4-(methoxyimino)-2-pyrrolidinecarboxylic acid | HCID 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-methyloxime | HCID 58714521 | 31% |
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
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07115639B2 |
| Source dataset | uspto-grants-2006_10 |
| ORD ID | ord-5ca02eb674b04e83a1b1ea79c70f3835 |
| Source note | uspto-grants-2006_10 |