Propargylamine → 6-((6-((Biotinoyl)amino)hexanoyl)amino)hexanoyl propargyl amine

Participants

Role	Name	HCID	Charge
Reactant	Propargylamine	HCID 239041	—
Reactant	N-(6-((2,5-Dioxopyrrolidin-1-yl)oxy)-6-oxohexyl)-6-((5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno(3,4-d)imidazol-4-yl)pentanoyl)amino)hexanamide	HCID 16219024	—
Solvent	Dimethylformamide	HCID 6228	—
Product	6-((6-((Biotinoyl)amino)hexanoyl)amino)hexanoyl propargyl amine	HCID 88234833	—

Reaction Steps

To a stirred solution of 6-((6-((Biotinoyl)amino)hexanoyl)amino)hexanoic acid, succinimidyl ester (biotin-NHS ester) (0.2 g, 0.35 mmol) in dry DMF (5 ml), propargyl amine (0.04 ml, 0.6 mmol) was added. A white precipitate formed within 15 min and the mixture was stirred overnight. The solvent was removed in vacuo and the compound was dissolved in CHCl3. Next the CHCl3 was slowly added to a stirred solution of hexane, forming a white precipitate, which on drying afforded 0.15 g (83%). Mass Spect. (FAB) MW 508 [M+]; NMR assigned. Crisp, G. T.; Gore, J. Syn. Comm. 1997, 27, 2203-2125

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06288221B1
Source dataset	uspto-grants-2001_09
ORD ID	ord-6d03c2dcbfae449498fd9071af32762a
Source note	uspto-grants-2001_09