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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 926006Generated: October 30, 2026

Trifluoroacetic acid → (1R,2R,5R)-5-(tert-butyldiphenylsilyloxy)-2-(hex-5-enyl(methyl)carbamoyl)cyclohexanecarboxylic acid

https://huagongshe.com/reaction/926006

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTrifluoroacetic acidHCID 6422—
Reactant(1R,2R,5R)-tert-butyl 5-(tert-butyldiphenylsilyloxy)-2-(hex-5-enyl(methyl)carbamoyl)cyclohexanecarboxylateHCID 58282736—
SolventDichloromethaneHCID 6344—
Product(1R,2R,5R)-5-(tert-butyldiphenylsilyloxy)-2-(hex-5-enyl(methyl)carbamoyl)cyclohexanecarboxylic acidHCID 5828272548%

Reaction Steps

To a solution of compound 39 (1.07 mmol) in anhydrous DCM (70 mL) was added TFA (42.6 mmol) slowly. The reaction mixture was stirred at room temperature for 16 hrs. The reaction mixture was concentrated and purified by silica gel chromatography (DCM/MeOH) to yield compound 40 as a yellow oil in 48% yield. MS (ESI, EI+): m/z=522 (MH+).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09284307B2
Source datasetuspto-grants-2016_03
ORD IDord-96056136ac7a407cb903af1fadabd026
Source noteuspto-grants-2016_03