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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2204954Generated: November 3, 2026

Toluene → diethyl (12R,16R)-12-amino-16-(dodecanoyloxy)-1,1-difluoro-11,19-dioxo-4,7,18-trioxa-14-thia-10-azatriacontylphosphonate

https://huagongshe.com/reaction/2204954

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTolueneHCID 1140—
ReactantPiperidineHCID 8082—
Reactantdiethyl(12R,16R)-12-(((9H-fluoren-9-yl)methoxy)carbonylamino)-16-(dodecanoyloxy)-1,1-difluoro-11,19-dioxo-4,7,18-trioxa-14-thia-10-azatriacontylphosphonateHCID 86678265—
SolventAcetonitrileHCID 6342—
Productdiethyl (12R,16R)-12-amino-16-(dodecanoyloxy)-1,1-difluoro-11,19-dioxo-4,7,18-trioxa-14-thia-10-azatriacontylphosphonateHCID 86678266—

Reaction Conditions

Temperature25 °C

Reaction Steps

To a solution of diethyl(12R,16R)-12-(((9H-fluoren-9-yl)methoxy)carbonylamino)-16-(dodecanoyloxy)-1,1-difluoro-11,19-dioxo-4,7,18-trioxa-14-thia-10-azatriacontylphosphonate (1 eq) was added 20% piperidine (50 eq) in acetonitrile The resulting mixture was stirred at 25° C. until the smarting material disappeared. 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 numberUS09365506B2
Source datasetuspto-grants-2016_06
ORD IDord-1be3111d65eb44699e8b0b429f138bcb
Source noteuspto-grants-2016_06