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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2407919Generated: October 30, 2026

Toluene → diethyl (14R,18R)-14-amino-18-(dodecyloxy)-13-oxo-3,6,9,20-tetraoxa-16-thia-12-azadotriacontylphosphonate

https://huagongshe.com/reaction/2407919

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTolueneHCID 1140—
ReactantPiperidineHCID 8082—
Reactantdiethyl (14R,18R)-14-(((9H-fluoren-9-yl)methoxy)carbonylamino)-18-(dodecyloxy)-13-oxo-3,6,9,20-tetraoxa-16-thia-12-azadotriacontylphosphonateHCID 86678304—
SolventAcetonitrileHCID 6342—
Productdiethyl (14R,18R)-14-amino-18-(dodecyloxy)-13-oxo-3,6,9,20-tetraoxa-16-thia-12-azadotriacontylphosphonateHCID 86678305—

Reaction Conditions

Temperature25 °C

Reaction Steps

To a solution of diethyl (14R,18R)-14-(((9H-fluoren-9-yl)methoxy)carbonylamino)-18-(dodecyloxy)-13-oxo-3,6,9,20-tetraoxa-16-thia-12-azadotriacontylphosphonate (1 eq) was added 20% piperidine (50 eq) in acetonitrile. The resulting mixture was stirred at 25° C. until the deprotection completed. To the mixture was added toluene and then concentrated en vaccuo. The crude mixture was purified by flash chromatography on a COMBIFLASH® system (ISCO) using 100% EtOAc then 0-10% MeOH/DCM to give the product as a colorless oil.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08808703B2
Source datasetuspto-grants-2014_08
ORD IDord-204e826aa4164deca541430939f790e3
Source noteuspto-grants-2014_08