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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1020139Generated: October 29, 2026

Ethyl Acetate → Tert-butyl 3-(4-carbamoyl-3-fluorophenylamino)-2-(4-(hydroxymethyl)phenyl)-3-oxopropylcarbamate

https://huagongshe.com/reaction/1020139

Reaction equation

Participants

RoleNameHCIDCharge
ReactantEthyl AcetateHCID 8857—
ReactantTetrabutylammonium FluorideHCID 2724141—
ReactantTert-butyl 3-(4-carbamoyl-3-fluorophenylamino)-3-oxo-2-(4-((triisopropylsilyloxy)methyl)phenyl)propylcarbamateHCID 59563790—
SolventTetrahydrofuranHCID 8028—
ProductTert-butyl 3-(4-carbamoyl-3-fluorophenylamino)-2-(4-(hydroxymethyl)phenyl)-3-oxopropylcarbamateHCID 59563726—

Reaction Conditions

Temperature0 °C

Reaction Steps

To tert-butyl 3-(4-carbamoyl-3-fluorophenylamino)-3-oxo-2-(4-((triisopropylsilyloxy)methyl)phenyl)propylcarbamate (E337) in THF under N2 at 0° C. was added TBAF, and the solution was stirred for 30 min at 0° C. The reaction was warmed to room temperature and stirred another 3.5 h. The compound was poured into EtOAc and washed with NH4Cl(sat), dried (MgSO4), filtered, and evaporated. Column chromatography (SiO2, 0-20% MeOH/CH2Cl2 gradient) gave pure tert-butyl 3-(4-carbamoyl-3-fluorophenylamino)-2-(4-(hydroxymethyl)phenyl)-3-oxopropylcarbamate (E337-1)

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08716310B2
Source datasetuspto-grants-2014_05
ORD IDord-f0f724b4924442018d4bf39a6aed8959
Source noteuspto-grants-2014_05