N-(tert-butoxycarbonyl)glycine → 4-{[(2S,4EZ)-2-(5-{[(tert-butoxycarbonyl)amino]methyl}-1,2,4-oxadiazol-3-yl)-4-(methoxyimino)pyrrolidinyl]carbonyl}-1,1'-biphenyl

Participants

Role	Name	HCID	Charge
Reactant	N-(tert-butoxycarbonyl)glycine	HCID 78288	—
Reactant	(2S,4EZ)-1-([1,1'-biphenyl]-4-ylcarbonyl)-N'-hydroxy-4-(methoxyimino)-2-pyrrolidinecarboximidamide	HCID 90995821	—
Product	4-{[(2S,4EZ)-2-(5-{[(tert-butoxycarbonyl)amino]methyl}-1,2,4-oxadiazol-3-yl)-4-(methoxyimino)pyrrolidinyl]carbonyl}-1,1'-biphenyl	HCID 58714549	80%

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 [(tert-butoxycarbonyl)amino]acetic acid, the title compound was obtained in 80% yield (78.2% purity by HPLC).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07115639B2
Source dataset	uspto-grants-2006_10
ORD ID	ord-91536d82184c4d418ef006075c6e22c8
Source note	uspto-grants-2006_10