Diisopropylethylamine → (9H-fluoren-9-yl)methyl ((11S,14R,18R)-1-(diethoxyphosphoryl)-18-dodecanamido-11-methyl-13-oxo-3,6,9,20-tetraoxa-16-thia-12-azadotriacontan-14-yl)carbamate

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	(R)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(((R)-2-dodecanamido-3-(dodecyloxy)propyl)thio)propanoic acid	HCID 67402076	—
Reactant	(S)-diethyl (2-(2-(2-(2-aminopropoxy)ethoxy)ethoxy)ethyl)phosphonate	HCID 86678313	—
Solvent	Dichloromethane	HCID 6344	—
Product	(9H-fluoren-9-yl)methyl ((11S,14R,18R)-1-(diethoxyphosphoryl)-18-dodecanamido-11-methyl-13-oxo-3,6,9,20-tetraoxa-16-thia-12-azadotriacontan-14-yl)carbamate	HCID 131731789	—

Reaction Steps

To a solution of (R)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(((R)-2-dodecanamido-3-(dodecyloxy)propyl)thio)propanoic acid (1 eq, from example 26, step 8) and HBTU (1.2 eq) in DCM (0.06 M) was added DIEA (3.5 eq), followed by (S)-diethyl (2-(2-(2-(2-aminopropoxy)ethoxy)ethoxy)ethyl)phosphonate (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-50b6f2825b724459b7b52a6c940af04e
Source note	uspto-grants-2014_08