4-(Hydroxymethyl)benzoic acid → (3Ez,5s)-1-([1,1'-biphenyl]-4-ylcarbonyl)-5-{5-[4-(hydroxymethyl)phenyl]-1,2,4-oxadiazol-3-yl}-3-pyrrolidinone o-methyloxime

Participants

Role	Name	HCID	Charge
Reactant	4-(Hydroxymethyl)benzoic acid	HCID 76360	—
Reactant	(2S,4EZ)-1-([1,1'-biphenyl]-4-ylcarbonyl)-N'-hydroxy-4-(methoxyimino)-2-pyrrolidinecarboximidamide	HCID 90995821	—
Product	(3Ez,5s)-1-([1,1'-biphenyl]-4-ylcarbonyl)-5-{5-[4-(hydroxymethyl)phenyl]-1,2,4-oxadiazol-3-yl}-3-pyrrolidinone o-methyloxime	HCID 58714546	—

Reaction Steps

Following the general method as outlined in Example 15, starting from (2S,4EZ)-1-([1,1′-biphenyl]-4-ylcarbonyl)-N′-hydroxy-4-(methoxyimino)-2-pyrrolidinecarboximidamide (Intermediate 8) and 4-(hydroxymethyl)benzoic acid, the title compound was obtained in 54% purity by HPLC. MS(ESI+): m/z=469.4.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07115639B2
Source dataset	uspto-grants-2006_10
ORD ID	ord-85b0f57985094d85823c83374a576603
Source note	uspto-grants-2006_10