N-Hydroxysuccinimide → N,N'-Bis-(9-Fluorenylmethyloxycarbonyl)-D-Lysyloxy Succinimide

Participants

Role	Name	HCID	Charge
Reactant	N-Hydroxysuccinimide	HCID 80170	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride	HCID 2723939	—
Reactant	Fmoc-D-lys(fmoc)-OH	HCID 22816294	—
Solvent	N,N-dimethylformamide ethyl acetate	HCID 22989253	—
Product	N,N'-Bis-(9-Fluorenylmethyloxycarbonyl)-D-Lysyloxy Succinimide	HCID 22816295	—

Reaction Steps

To a stirred solution of N,N'-bis-(9-fluorenylmethyloxycarbonyl)-D-lysine (12.0 g) in 360 ml of an ethylacetate:dimethylformamide (35:1) mixture are added N-hydroxysuccinimide (3.1 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (5.2 g) and diisopropylethylamine (2.0 ml). After 15 hours the solution is washed successively with dilute hydrochloric acid, water, saturated sodium bicarbonate solution, and brine, dried over magnesium sulfate, and concentrated in vacuo to about 20 ml. The solution is added to hexane (1 l.) and the precipitate is collected and dried to afford the title compound.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US04272525
Source dataset	uspto-grants-1981_06
ORD ID	ord-411aefadc51d4b08b86231303004d859
Source note	uspto-grants-1981_06