Diisopropylethylamine → 9h-fluoren-9-ylmethyl{(1S)-4-amino-1-[({(2s)-2,5-bis[(tert-butoxycarbonyl)amino]pentyl}amino)carbonyl]-4-oxobutyl}carbamate

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	N2-((9H-Fluoren-9-ylmethoxy)carbonyl)-L-glutamine	HCID 2724775	—
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	tert-Butyl {(4S)-5-amino-4-[(tert-butoxycarbonyl)amino]pentyl}carbamate	HCID 57440197	—
Solvent	Dimethylformamide	HCID 6228	—
Product	9h-fluoren-9-ylmethyl{(1S)-4-amino-1-[({(2s)-2,5-bis[(tert-butoxycarbonyl)amino]pentyl}amino)carbonyl]-4-oxobutyl}carbamate	HCID 70806689	—

Reaction Steps

129 mg (0.34 mmol) of HATU and 133 mg (0.95 mmol) of N,N-diisopropylethylamine are added to a solution of 100 mg (0.27 mmol) of N2-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-glutamine and 112 mg (0.35 mmol) of tert-butyl{(4S)-5-amino-4-[(tert-butoxycarbonyl)amino]pentyl}carbamate (Example 86A) 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-81743811b6c4430b81ef7e79aebcb1cc
Source note	uspto-grants-2008_11