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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 77031Generated: October 29, 2026

Trifluoroacetic acid → (R)-3-((S)-2-amino-phenylpropanoyloxy)-1-(2-phenoxyethyl)-1-azonia-bicyclo[2.2.2]octane trifluoroacetate trifluoroacetate

https://huagongshe.com/reaction/77031

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTrifluoroacetic acidHCID 6422—
ReactantHCID 68468848HCID 68468848—
SolventDichloromethaneHCID 6344—
Product(R)-3-((S)-2-amino-phenylpropanoyloxy)-1-(2-phenoxyethyl)-1-azonia-bicyclo[2.2.2]octane trifluoroacetate trifluoroacetateHCID 8664322043%

Reaction Steps

To a solution of (R)-3-((S)-2-tertbutoxycarbonylamino-phenylpropanoyloxy)-1-(2-phenoxyethyl)-1-azonia-bicyclo[2.2.2]octane bromide (I148) (0.53 mmol) in DCM (5 mL), is added trifluoroacetic acid (0.50 mL, 4.41 mmol) and the mixture stirred at RT overnight. The solvent is evaporated and the resulting crude is purified by preparative LC-MS in order to obtain the title compound as a brown gummy solid (112 mg, 43% overall yield, trifluoroacetate salt and trifluoroacetate anion, single diastereoisomer).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08835682B2
Source datasetuspto-grants-2014_09
ORD IDord-92d71e6e05c24c478187cc0b30fb9e52
Source noteuspto-grants-2014_09