Diisopropylethylamine → N5-[(Benzyloxy)carbonyl]-N2-(tert-butoxycarbonyl)-L-ornithyl-N5-[(benzyloxy)carbonyl]-N-(2-{[(benzyloxy)carbonyl]amino}ethyl)-L-ornithinamide

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	(2S)-5-{[(benzyloxy)carbonyl]amino}-2-{[(tert-butoxy)carbonyl]amino}pentanoic acid	HCID 7269338	—
Reactant	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Reactant	Benzyl{(4s)-4-amino-5-[(2-{[(benzyloxy)carbonyl]amino}ethyl)amino]-5-oxopentyl}carbamate	HCID 131727157	—
Solvent	Dimethylformamide	HCID 6228	—
Product	N5-[(Benzyloxy)carbonyl]-N2-(tert-butoxycarbonyl)-L-ornithyl-N5-[(benzyloxy)carbonyl]-N-(2-{[(benzyloxy)carbonyl]amino}ethyl)-L-ornithinamide	HCID 86619431	—

Reaction Steps

350 mg (0.92 mmol) of HATU and 330 mg (2.56 mmol) of N,N-diisopropylethylamine are added to a solution of 320 mg (0.88 mmol) of N5-[(benzyloxy)carbonyl]-N2-(tert-butoxycarbonyl)-L-ornithine and 350 mg (0.73 mmol) of benzyl{(4S)-4-amino-5-[(2-{[(benzyloxy)carbonyl]amino}ethyl)amino]-5-oxopentyl}carbamate (Example 122A) in 5 ml of anhydrous DMF at 0° C. The reaction mixture is stirred at RT for 15 h. The solvent is then evaporated and the residue is stirred with water, collected by filtration and dried under high vacuum.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07446102B2
Source dataset	uspto-grants-2008_11
ORD ID	ord-fee326e019414238842ceb08553e05da
Source note	uspto-grants-2008_11