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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 735705Generated: October 29, 2026

Tetrabutylammonium Fluoride → 2-(1-(bis(tert-butoxycarbonyl)amino)isoquinolin-6-ylamino)-2-(4-(2-hydroxypropyl)phenyl)-N-(3-nitrobenzyl)acetamide

https://huagongshe.com/reaction/735705

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTetrabutylammonium FluorideHCID 2724141—
Reactant2-(1-(bis(tert-butoxycarbonyl)amino)isoquinolin-6-ylamino)-2-(4-(2-(tert-butyldimethylsilyloxy)propyl)phenyl)-N-(3-nitrobenzyl)acetamideHCID 57842634—
SolventTetrahydrofuranHCID 8028—
Product2-(1-(bis(tert-butoxycarbonyl)amino)isoquinolin-6-ylamino)-2-(4-(2-hydroxypropyl)phenyl)-N-(3-nitrobenzyl)acetamideHCID 5784273326%

Reaction Conditions

Temperature35 °C

Reaction Steps

To a solution of 77E (172 mg, 0.215 mmol) in 3 mL THF, was added a solution of TBAF (1M in THF, 1 mL, 1 mmol). The mixture was stirred at 35° C. for 17 h, then concentrated. The residue was dissolved in EtOAc, washed with water (2×) and brine, dried (Na2SO4) and concentrated. Purification by flash chromatography (0 to 100% EtOAc/hexanes) afforded 38 mg (26%) of 77F as a yellow glass. MS (ESI) m/z 686.4 (M+H)+.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07592331B2
Source datasetuspto-grants-2009_09
ORD IDord-0ceb246662064ed5b313039a700e59ab
Source noteuspto-grants-2009_09