Diisopropylethylamine → (15R,19R)-tert-butyl 15-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-19-(dodecyloxy)-14-oxo-4,7,10,21-tetraoxa-17-thia-13-azatritriacontan-1-oate

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 2733084	—
Reactant	tert-Butyl 12-amino-4,7,10-trioxadodecanoate	HCID 16218573	—
Reactant	(R)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(((R)-2,3-bis(dodecyloxy)propyl)thio)propanoic acid	HCID 67400890	—
Solvent	Dichloromethane	HCID 6344	—
Product	(15R,19R)-tert-butyl 15-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-19-(dodecyloxy)-14-oxo-4,7,10,21-tetraoxa-17-thia-13-azatritriacontan-1-oate	HCID 86678318	—

Reaction Steps

To a solution of (R)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(((R)-2,3-bis(dodecyloxy)propyl)thio)propanoic acid (1 eq, from example 20, step 5) and HBTU (1.2 eq) in DCM (0.06 M) was added DIEA (3.5 eq), followed by tert-butyl 3-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)propanoate (1.2 eq). The reaction was stirred at room temperature for 2 hours. The crude mixture was purified by flash chromatography on a COMBIFLASH® system (ISCO) using 0-5% MeOH/DCM to give the title product as a white solid.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08808703B2
Source dataset	uspto-grants-2014_08
ORD ID	ord-ad9e66deb0134a07a96f0dbddefb141e
Source note	uspto-grants-2014_08