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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1096849Generated: October 25, 2026

Tetrabutylammonium Fluoride → 6-[Cyclopropyl-(2,3-dichlorobenzyl)carbamoyl]-7-[4-(3-hydroxypropyl)thiazol-2-yl]-3,9-diazabicyclo[3.3.1]non-6-ene-3,9-dicarboxylic acid di-tert-butyl ester

https://huagongshe.com/reaction/1096849

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTetrabutylammonium FluorideHCID 2724141—
Reactant7-{4-[3-(tert-Butyldimethylsilanyloxy)propyl]thiazol-2-yl}-6-[cyclopropyl-(2,3-dichlorobenzyl)carbamoyl]-3,9-diazabicyclo[3.3.1]non-6-ene-3,9-dicarboxylic acid di-tert-butyl esterHCID 68569724—
SolventTetrahydrofuranHCID 8028—
SolventEthyl AcetateHCID 8857—
Product6-[Cyclopropyl-(2,3-dichlorobenzyl)carbamoyl]-7-[4-(3-hydroxypropyl)thiazol-2-yl]-3,9-diazabicyclo[3.3.1]non-6-ene-3,9-dicarboxylic acid di-tert-butyl esterHCID 6857077496.1%

Reaction Steps

A sol. of compound E3 (1.23 g, 1.50 mmol) and TBAF (1.0 M in THF, 1.88 mL, 1.88 mmol) in THF (20 mL) was stirred at 0° C. for 3.5 h. The mixture was diluted with EtOAc and was then washed with brine (4×). The org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (EtOAc/heptane 1:4→1:2→1.1→EtOAc) yielded the title compound (1.02 g, 96%). LC-MS: tR=1.11 min, ES+: 707.33.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08138340B2
Source datasetuspto-grants-2012_03
ORD IDord-58a3abf6af784faea4cb95b9bc4ccb92
Source noteuspto-grants-2012_03